Azolo[1,4]diazepines: the methods of synthesis and structural modification

Authors

  • S. V. Kemskii Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • A. V. Bolbut Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • Yu. V. Dmytriv NTUU «Igor Sikorsky Kyiv Polytechnic Institute», Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.17.911

Keywords:

pyrazolodiazepines, imidazodiazepines, synthesis, cyclocondensation, structural modification

Abstract

The literature relating to the methods of synthesis and chemical transformations of azolo[1,4]diazepines (pyrazolo-, imidazo-, triazolo-, isoxazolo-, oxazolo-, isothiazolo- and thiazolodiazepines) currently known have been generalized and systematized. Their role as important substances for the design of compounds with a great pharmacological potential has been noted. The methods of synthesis of pyrazolo[3,4-e][1,4]diazepines, pyrazolo[4,3-e][1,4]diazepines and tri- and tetracyclic pyrazolo[1,4]diazepines based on formation of the diazepine ring in most cases due to transformations of multifunctional pyrazole derivatives have been described in detail. A significant emphasis is focused on the structural functionalization of pyrazolo[1,4]diazepines; this functionalization is a powerful tool to design attractive synthetic and biological derivatives. On the examples of 7-hydroxypyrazole[3,4-e][1,4]diazepines the effect of the reaction conditions, electronic and steric parameters, which control the processes of functionalization of the diazepine nucleus with SH-, NH- and C- nucleophilic reagents, is described. The synthetic potential of 7-arylpyrazole[4,3-e][1,4]diazepin-4-ones as key structures for their direct functionalization in position 4 with chloro-, methylthio-, amino- and hydrazino groups is shown. The methods of preparation and some chemical transformations of imidazo[1,4]diazepines, in particular imidazo[4,5-e][1,4]diazepin-8-ones and 5,8-diones, which in recent years attract great attention of researchers, have been analyzed.

Downloads

Download data is not yet available.

References

  1. Sedative but not anxiolytic properties of benzodiazepines are mediated by the GABA(A) receptor alpha1 subtype / R. M. Mc Kernan, T. W. Rosahl, D. S. Reynolds et al. // Nature Neuroscience. – 2000. – Vol. 3, Issue 6. – Р. 587–592.
  2. Sternbach, L. H. The benzodiazepine story / L. H. Sternbach // J. Med. Chem. – 1979. – Vol. 22, Issue 1. – Р. 1–7. doi : 10.1021/jm00187a001.
  3. Clinical features and management of intoxication due to hallucinogenic drugs / J. B. Leikin, A. J. Krantz, M. Zell–Kanter et al. // Med. Toxicol. Adverse Drug Exp. – 1989. – Vol. 4, Issue 5. – Р. 324–350. doi : 10.1007/bf03259916.
  4. Miller, N. S. Benzodiazepines: reconsidered / N. S. Miller, M. S. Gold // Adv. Alcohol Subst Abuse. – 1990. – Vol. 8, Issue 3–4. – Р. 67–84. doi : 10.1300/j251v08n03_06.
  5. Shorter, E. Benzodiazepines / E. Shorter // A Historical Dictionary of Psychiatry. –New York:OxfordUniversityPress, 2005. – P. 41–42.
  6. King, M. B. Is there still a role for benzodiazepines in general practice? / M. B. King // Br. J. Gen. Pract. – 1992. – Vol. 42, Issue 358. – P. 202–205.
  7. Lemmer, B. The sleep–wake cycle and sleeping pills / B. Lemmer // Physiol. Behav. – 1989. – Vol. 90, Issue 2–3. – Р. 285–293.
  8. DeWald, H. A. Pyrazolodiazepines. 2. 4–Aryl–1,3–dialkyl–6,8–dihydropyrazolo[3,4–e][1,4]diazepin–7(1H)–ones as antianxiety and anticonvulsant agents. / H. A. DeWald, S. Lobbestae, D.E. Butler// J. Med. Chem. – 1977. – Vol. 20, Issue 12. – Р. 1562–1569. doi : 10.1021/jm00222a005
  9. Field anesthesia of free–living mountain gorillas (Gorilla gorilla beringei) from the Virunga Volcano region, Central Africa / J. M. Sleeman, K. Cameron, A. B. Mudakikwa et al. // J. Zoo Wildlife Med. – 2000. – Vol. 31, Issue 1. – Р. 9–14. doi : 10.1638/1042–7260(2000)031[0009:faoflm]2.0.co;2.
  10. Anesthesia of polar bears (Ursus maritimus) with zolazepam–tiletamine, medetomidine–ketamine, and medetomidine–zolazepam–tiletamine / M. R. Cattet, N. A. Caulkett, S. C. Polischuk, M. A. Ramsay // J. Zoo Wildlife Med. – 1999. – Vol. 30, Issue 3. – Р. 354–360.
  11. Fitzgerald, J. E. Carcinogenicity studies in rodents and ripazepam, a minor tranquilizing agent / J. E. Fitzgerald, F. A. dela Iglesia, E. J. McGuire // Fundamental and Applied Toxicol. – 1984. – Vol. 4, Issue 2. – Р. 178–190. doi : 10.1016/0272–0590(84)90118–0.
  12. Synthesis and interaction of 5–(substituted–phenyl)–3–methyl–6,7–dihydropyrazolo[4,3–e][1,4]diazepin–8(7H)–ones with benzodiazepine receptors in rat cerebral cortex / P. G. Baraldi, S. Manfredini, V. Periotto et al. // J. Med. Chem. – 1985. – Vol. 28, Issue 5. – Р. 683–685. doi : 10.1021/jm50001a025.
  13. Renger, B. DirekteN–Arylierung von Amiden: Eine Verbesserung der Goldberg–Reaktion / B. Renger // Synthesis. – 1985. – Issue 09. – Р. 856–860. doi : 10.1055/s–1985–31364.
  14. Katz, R. J. Effects of zometapine, a structurally novel antidepressant, in an animal model of depression / R. J. Katz // Pharmacol. Biochem. Behav. – 1984. – Vol. 21, Issue 4. – Р. 487–490. doi : 10.1016/s0091–3057(84)80027–1.
  15. Hock, F. J. Functional activity in the brain of socially deprivated rats produced by an active avoidance test after razobazam (Hoe 175) treatment: a 2–deoxyglucose study. / F. J. Hock, H. Scheich / Behavioural and Neural Biology. – 1986. – Vol. 46, Issue 3. – Р. 398–409. doi : 10.1016/s0163–1047(86)90401–2.
  16. Pat. WO2007040435 (A1) (2007). Novel 5,6–dihydropyrazolo[3,4–e] [l,4]diazepin–4(H)–one derivatives for the treatment of asthma and chronic obstructive pulmonary disease / K. Henriksson, A. Lisius, P. Sjo, P. Storm; Astra Zeneca Ab. – Declared 2.10.2006; published 12.04.2007.
  17. Pat. US 20070197608 A1. Piperazine as oxitocin agonists / P. Hudson, G. P. W. Pitt, A. R. Batt, M. B. Roe. – Declared 02.09.2004; published 23.08. 2007.
  18. Ujjinamatada, R. K. Design of inhibitors against guanase: Synthesis and biochemical evaluation of analogues of azepinomycin / R. K. Ujjinamatada, A. Bhan, R. S. Hosmane // Bioorg. Med. Chem. Lett. – 2006. – Vol. 16, Issue 21. – Р. 5551–5554. doi : 10.1016/j.bmcl.2006.08.033.
  19. A novel transition state analog inhibitor of guanase based on azepinomycin ring structure: Synthesis and biochemical assessment of enzyme inhibition. / S. Chakraborty, N. H. Shah, J. C. Fishbein, R. S. Hosmane // Bioorg. Med. Chem. Lett. – 2011. – Vol. 21, Issue 2. – Р. 756–759. doi : 10.1016/j.bmcl.2010.11.109.
  20. Analogs of iso–azepinomycin as potential transition–state analog inhibitors of guanase: Synthesis, biochemical screening, and structure–activity correlations of various selectively substituted imidazo[4,5–e][1,4]diazepines / S. Tantravedi,S. Chakraborty, N. H. Shah et al. // Bioorg. Med. Chem. – 2013. – Vol. 21, Issue 17. – Р. 4893–4903. doi : 10.1016/j.bmc.2013.06.069.
  21. Pat. US 3558605 (1971). Pyrazolo[3,4–e][1,4]diazepin–7–(1Н)–one compounds / D. E. Butler, H. A. DeWald; ParkeDavis. – Declared 14.05.1969; published 26.01.1971.
  22. Pat. US 3660425 (1972). Certain 5–amino–4–aroylpyrazoles / D. E. Butler, H. A. DeWald; ParkeDavis. – Declared 30.03.1970; published 2.05.1972.
  23. DeWald, H. A. Pyrazolodiazepines. III. 4–Aryl–1,6,7,8–tetrahydro–1,3–dialkylpyrazolo[3,4–e][1,4]diazepines as antidepressant agents / H. A. DeWald, S. Lobbestael // J. Med. Chem. – 1981. – Vol. 24, Issue 8. – Р. 982–987. doi : 10.1021/jm00140a013.
  24. DeWald, H. A. The synthesis of 4–(o–fluorophenyl)–6,8–dihydro–3,8–dimethyl–pyrazolo[3,4–e][1,4]diazepin–7(1H)one, a metabolite of zolazepam / H. A. DeWald // J. Het. Chem. – 1974. – Vol. 11, Issue 6. – Р. 1061–1062. doi : 10.1002/jhet.5570110637.
  25. Конденсовані піримідинові системи. 9. Синтез похідних піразоло[3,4–e][1,4]діазепіну на основі продуктів гідролітичного розщеплення 5–заміщених 1,2–дигідро–4Н–піразоло[3,4–d]піримідин–4–онів/ А. В. Больбут, А. А. Ліщинський, І. М. Мельничук, М. В. Вовк // Журн. орг. та фарм. хімії. – 2010. – Vol. 8, № 1. – Р. 54–57.
  26. Bol’but, A. V. Synthesis of New Di–, Tetra–, and Hexahydropyrazolo[3,4–e][1,4]diazepsne Derivatives / A. V. Bol’but, S. V. Kemskii, M. V. Vovk // Rus. J. Org. Chem. – 2012. – Vol. 48, Issue 7. – Р. 991–1002. doi : 10.1134/s1070428012070172.
  27. Конденсовані піримідинові системи. 8. Гідролітичне розщеплення 5–алкіл–1,5–дигідро–4Н–піразоло[3,4–d]піримідин–4–онів як зручний метод синтезу N–алкіламідів 5–аміно–4–піразолкарбонових кислот / А. В. Больбут, А. А. Ліщинський, І. М. Мельничук, М. В. Вовк // Журн. орг. фарм. хімії. – 2007. – Vol. 5, № 3. – Р. 64–66.
  28. Больбут, А. В. 5–Амино–N–(2,2–диалкоксиэтил)пиразоло–4–карбоксамиды в синтезе 7–сульфанил–5,6,7,8–тетра–1Н–пиразоло[3,4–е][1,4]диазепин–4–онов / А. В. Больбут, С. В. Кемский, М. В. Вовк // Журн. орган. химии. – 2014. – Т. 50, № 5. – С. 697–702.
  29. Кемський, С. В. Синтез 7–карбоксиалкілтіо–5,6,7,8–тетрагідро–1Н–піразоло[3,4–e][1,4]діазепін–4–онів / С. В. Кемський, А. В. Больбут, М. В. Вовк // Журн. орган. фарм. хімії. – 2014. – Т. 12, № 2. – С. 27–31.
  30. Синтез 4–оксо–1,4,5,6,7,8–гексагидро–1Н–пиразоло[3,4–е][1,4]диазепин–7–карбонитрилов, –карбоксамидов и –карбоновых кислот / С. В. Кемский, А. В. Больбут, В. В. Пироженко, М. В. Вовк // Журн. орган. химии. – 2014. – Т. 50, № 11. – С. 1652–1656.
  31. 7–N–Ацилфункціоналізовані похідні піразоло[3,4–e][1,4]діазепін–4–онів / С. В. Кемський, А. В. Больбут, Ю. С. Бойко та ін. // Укр. хим. журн. – 2015. – Т. 81, № 2. – С. 124–128.
  32. Кемский, С. В. Синтез 4–гидразино–1,6–дигидропиразоло[3,4–е][1,4]диазепинов и их гидролитическая рециклизация в 5–амино–4–(1,2,4–триазин–3–ил)–1Н–пиразолы / С. В. Кемский, А. В. Больбут, М. В. Вовк // Журн. орган. химии. – 2015. – Т. 51, № 10. – С. 1510–1516.
  33. 4–Амінозаміщені 1,6–дигідропіразоло[3,4–е][1,4]діазепіни : синтез, ЯМР–спектральне та квантово–хімічне дослідження / С. В. Кемський, Ю. С. Бойко, А. В. Больбут та ін. // Журн. орган. фарм. хімії. – 2016. – Т. 1, № 3. – С. 43–51.
  34. Синтез новой гетероциклической системы – пиразоло[3’,4’:5,6][1,4]диазепино[7,1–b]хиназолина / С. В. Кемский, Е. В. Гринишин, А. В. Больбут, М. В. Вовк // Журн. орган. химии.– 2016. – Т. 52, № 4. – С. 619–620.
  35. Pyrazolodiazepines. 1,3–(and 2,3)–dialkyl–4,6–dshydropyrazolo[3,4–e][1,4]diazepin–7(1H)ones as Antianxiety and Anticonvulsant Agents / H. A. DeWald, I. C. Nordin, Y. J. L’Italien et al. // J. Med. Chem. – 1973. – Vol. 16, Issue 12. – Р. 1346–1354. doi : 10.1021/jm00270a007.
  36. Synthesis and Reactivity of Fyro[2,3–e]pyrrolo[1.2–a][1.4]diazepin–9–one / О. Migliara, А. Flugy, V. Novara, M. Gagliano // Farmaco. – 1992. – Vol. 47. – P. 111–120.
  37. Discovery of potent, selective, bioavailable phosphodiesterase 2 (PDE2) inhibitors active in an osteoarthritis pain model. Part I : Transformation of selective pyrazolodiazepinone phosphodiesterase 4 (PDE4) inhibitors into selective PDE2 inhibitors / M. S. Plummer, J. Cornicelli, H. Roark et al. // Bioorg. Med. Chem. Lett. – 2013. – Vol. 23, Issue 11. – P. 3438–3442. doi : 10.1016/j.bmcl.2013.03.072.
  38. Discovery of potent selective bioavailable phosphodiesterase 2 (PDE2) inhibitors active in an osteoarthritis pain model. Part II: Optimization studies and demonstration of in vivo efficacy / M. S. Plummer, J. Cornicelli, H. Roark et al. // Bioorg. Med. Chem. Lett. – 2013. – Vol. 23, Issue 11. – P. 3443–3447. doi : 10.1016/j.bmcl.2013.03.082.
  39. Pat. WO 2012168817 (A1) (2012). Pyrazolo[3,4–d]pyrimidine compounds and their use as pde2 inhibitors and/or Cyp3a4 inhibitors / C. J. Helal, T. A. Chappie, J. M. Humphrey; Pfizer Inc. – Declared 7.06.2011; published 24.05.2012.
  40. Synthesis and structure–activity relationships of pyrazolodiazepine derivatives as human P2X7 receptor antagonists / J.–Y. Lee, W. J. Cho, H. Ko, Y.–C. Kim // Bioorg. Med. Chem. Lett. – 2009. – Vol. 19, Issue 21. – P. 6053–6058. doi : 10.1016/j.bmcl.2009.09.053.
  41. Lee, J.–Y. Combinatorial Library Synthesis and Biological Evaluation of Pyrazolo[4,3–e][1,4]diazepine as a Potential Privileged Structure / J.–Y. Lee, Y.–C. Kim // Chem. Med. Chem. – 2009. – Vol. 4, Issue 5. – P. 733–737. doi : 10.1002/cmdc.200800453.
  42. Discovery and structure–activity relationships of pyrazolodiazepine derivatives as the first small molecule agonists of the Drosophila sex peptide receptor / J.–H. Kim, P.–H. Jeong, J.–Y. Lee et al. // Bioorg. Med. Chem. Lett. – 2015. – Vol. 23, Issue 8. – P. 1808–1812. doi : 10.1016/j.bmc.2015.02.035.
  43. Mahdi, O., Synthese de cyclodipeptides de β–amino asides pyrazoliques / O. Mahdi, J.–P. Lavergne, P. Viallefont et al. // Bull. Soc. Chim. Belg. – 1995 – Vol. 104, Issue 1. – P. 31–38.
  44. Synthese de cyclodipeptides a sept chainons a partir de β–amino asides pyrazoliques / O. Mahdi, J.–P. Lavergne, P. Viallefont et al. // Bull. Soc. Chim. Fr. – 1995. – Vol. 132, Issue 7. – P. 675–680.
  45. Synthesis of novel pyrazolopyrrolopyrazines, potential analogs of sildenafil / M. Kopp, J.–C. Lancelot, P. Dallemagne,S. Rault// J. Heterocycl. Chem. – 2001. – Vol. 38, Issue 5. – P. 1045–1050. doi : 10.1002/jhet.5570380506.
  46. Synthesis and Evaluation of Polycyclic Pyrazolo[3,4–d]pyrimidines as PDE1 and PDE5 cGMP Phosphodiesterase Inhibitors / Y. Xia,S. Chackalamannil, M. Czarniecki et al. // J. Med. Chem. – 1997. – Vol. 40, Issue 26. – P. 4372–4377. doi : 10.1021/jm970495b.
  47. Huppatz, J. L. Systemic fungicides. The synthesis of certain pyrazole analogues of carboxin / J. L. Huppatz // Aust. J. Chem. – 1983. – Vol. 36, Issue 1. – P. 135–147. doi : 10.1071/ch9830135.
  48. The synthesis of pyrazolo[4,3–e][1,4]diazepines / V. Sprio,S. Caronna, O. Migliara et al. // Farmaco – 1989 – Vol. 44, Issue 9 – P. 809–818.
  49. Raeppel, S. L. Design and synthesis of constrained analogs of LCRF–0004 as potent RON tyrosine kinase inhibitors / S. L. Raeppel, E. Therrien, F. Raeppel // Bioorg. Med. Chem. Lett. – 2015. – Vol. 25, Issue 17. – P. 3706–3710. doi : 10.1016/j.bmcl.2015.06.034.
  50. Identification of a novel series of potent RON receptor tyrosine kinase inhibitors / S. L. Raeppel, F. Gaudette, M. Mannion et al. // Bioorg. Med. Chem. Lett. – 2010. – Vol. 20, Issue 9. – P. 2745–2749. doi : 10.1016/j.bmcl.2010.03.073.
  51. Рat. WO 2007/107005 (A1) (2007). Inhibitors of protein tyrosine kinase activity / O. M. Saavedra, S. W. Claridge, L. Zhan et al; Methylgene Inc. – Declared 22.03.2007; published 27.09.2007.
  52. Reddy, N. R. A new entry to pyrazolo[4,3–e][1,4]diazepines. Facile synthesis of pyrazolo[4,3–e][1,4]diazepin–5,8–diones, 5,6,8–triones and pyrazolo[4,3–e]pyrrolo–[1,2–a][1,4]diazepin–5,10–diones / N. R. Reddy, G. M. Reddy, P. P. Reddy // J. Heterocycl. Chem. – 2005. – Vol. 42, Issue 4. – P. 675–678. doi : 10.1002/jhet.5570420429.
  53. A Practical Approach of Continuous Processing to High Energetic Nitration Reactions in Microreactors / G. Panke, T. Schwalbe, W. Stirner et al. // Synthesis. – 2003. – Issue 18. – P. 2827–2830. doi : 10.1055/s–2003–42491.
  54. Synthesis of pyrazolo[3,4–b][1,4]diazepines and pyrazolo[3,4–b]pyrazines / A. Colombo, J. Frigola, J. Parés, B. Andaluz // J. Heterocyclic Chem. – 1989. – Vol. 26, Issue 9. – P. 949–655.
  55. Взаимодействие 1,5,6,8–тетрагидро[3,4–е][1,4]диазепин–4,7–дионов с некоторими електрофильными реагентами / С. В. Кемский, А. В. Больбут, С. В. Шишкина и др. // Журн. орган. химии. – 2016. – Т. 52, № 8. – С. 1170–1175.
  56. Research on nitrogen heterocyclic compounds. XV. Synthesis of 1H,4H–pyrazolo[4,3–f]pyrrolo[1,2–a][1,4]diazepine derivatives / S. Massa, G. Stefancich, M. Artico, F. Corelli // J. Heterocycl. Chem. – 1984. – Vol. 21, Issue 6. – P. 1877–1880. doi : 10.1002/jhet.5570210658.
  57. New Four–Component Ugi–Type Reaction. Synthesis of Heterocyclic Structures Containing a Pyrrolo[1,2–a][1,4]diazepine Fragment / A. P. Ilyn, A. S. Trifilenkov, J. A. Kuzovkova et al. // J. Org. Chem. – 2005. – Vol. 70, Issue 4. – P. 1478–1481. doi : 10.1021/jo048204b.
  58. Furan ring opening–pyrrole ring closure: a new synthetic route to aryl(heteroaryl)annulated pyrrolo[1,2–a][1,4]diazepines / A. V. Butin, T. A. Nevolina, V. A. Shcherbinin et al. // Org. Biomol. Chem. – 2010. – Vol. 8, Issue 14. – P. 3316. doi : 10.1039/c002994g.
  59. Tumkevicius, S. Synthesis of 3,4–diamino–1H–pyrazolo[3,4–d]pyrimidines /S. Tumkyavichyus// Chem. Heterocycl. Comp. – 1996. – Vol. 32, Issue 6. – P. 716–720. doi : 10.1007/bf01164873.
  60. Masevicius, V. Synthesis of a novel heterocyclic system–pyrazolo[5,4,3–de]pyrimido[4,5–e][1,4]diazepine / V. Masevicius, R. Juskenas, S. Tumkevicius // Chem. Heterocycl. Comp. – 2007. – Vol. 43, Issue 12. – P. 1593–1594. doi : 10.1007/s10593–007–0247–y.
  61. Masevicius, V. Synthesis of novel pyrazolo[3,4–d]pyrimidines perifused with 1,4–diazepine, 1,4–thiazepine, and 1,2,4–triazepine rings / V. Masevicius, R. Juskenas, S. Tumkevicius // J. Heterocycl. Chem. – 2011. – Vol. 49, Issue 2. – P. 315–320. doi : 10.1002/jhet.724.
  62. Synthesis of pyrazole analogues of isoaptazepine / S. Massa, M. Artico, A. Mai, A. Mancuso // J. Heterocycl. Chem. – 1992. – Vol. 29, Issue 7. – P. 1851–1854. doi : 10.1002/jhet.5570290729.
  63. Coggins, A. J. One step protecting group–free synthesis of azepinomycin in water. / A. J. Coggins, D. A. Tocher, M. W. Powner // Org. Biomol. Chem. – 2015. – Vol. 13, Issue 11. – P. 3378–3381. doi : 10.1039/c5ob00210a.
  64. Investigations into specificity of azepinomycin for inhibition of guanase: Discrimination between the natural heterocyclic inhibitor and its synthetic nucleoside analogues / S. Chakraborty, N. H. Shah, J. C. Fishbein, R. S. Hosmane // Bioorg. Med. Chem. Lett. – 2012. – Vol. 22, Issue 23. – P. 7214–7218. doi : 10.1016/j.bmcl.2012.09.053.
  65. Fujii, T. Alternative syntheses of azepinomycin / T. Fujii, T. Saito, T. Fujisawa // Heterocycles. – 1988. – Vol. 27, Issue 5. – P. 1163. doi : 10.3987/com–88–4519.
  66. Fujii, T. Purines. LXIII. Syntheses of Azepinomycin, an Antitumor Antibiotic from Streptomyces Species, and Its 3–β–D–Ribofuranodise and Their 8–Imino Analogues / T. Fujii, T. Saito, T. Fujisawa // Chem. Pharm. Bull. – 1994. – Vol. 42, Issue 6. – P. 1231–1237. doi : 10.1248/cpb.42.1231.
  67. Fujii, T. Purines. VIII. An Improved procedure for the Synthesis of 9–Alkyladenines / T. Fujii // Chem. Pharm. Bull. – 1972. – Vol. 20, Issue 6. – P. 1334–1337. doi : 10.1248/cpb.20.1334.
  68. Fujii, T. Purines. II An Alternative Synthesis of 1–Alkoxy–9–alkyladenine Salts / T. Fujii, C. C. Wu, T. Itaya // Chem. Pharm. Bull. – 1971. – Vol. 19, Issue 7. – P. 1368–1373. doi : 10.1248/cpb.19.1368.
  69. Bridson, P. K. Synthesis of Deoxyazepinomycin / P. K. Bridson // Heterocycles. – 1994. – Vol. 38, Issue 5. – P. 1007. doi : 10.3987/com–93–6637.
  70. Ivanov, E. I. Novel synthesis of 4,5,7,8–tetrahydro–6H–imidazo[4,5–e]–[1,4]diazepine–5,8–dione. A cyclic xanthine homolog / E. I. Ivanov, G. D. Kalayanov // Chem. Heterocycl. Comp. – 1992. – Vol. 28, Issue 4. – P. 428–429. doi : 10.1007/bf00767004.
  71. Богатский, А. В. Синтез 1,4,7–триметил–4,5,7,8–тетрагидроимидазо[4,5–e][1,4]диазепин–5,8(6Н)–дионов – циклического гомолога кофеина / А. В. Богатский, Э. И. Иванов // Укр. хим. журн. – 1980. – Т. 46, № 10. – P. 1074–1075.
  72. Ivanov, I. E. Novel synthesis and reactions of 1,4,7–trimethyl–4,5,7,8–tetrahydro–6H–imidazo[4,5–e][1,4]diazepine–5,8–dione–a cyclic caffeine analog / E. I. Ivanov // Chem. Heterocycl. Comp. – 1998. – Vol. 34, Issue 6. – P. 719–722. doi : 10.1007/bf02252283.
  73. Иванов, Э. И. Синтез и свойства производных 1,4,7–триметил–4,5,7,8–тетрагидроимидазоло[4,5–e][1,4]диазепин–5,8–диона / Э. И. Иванов, А. В. Богатский, К. С. Захаров // Докл. Акад. Наук. – 1980. – Т. 255, № 3. – P. 591–595.
  74. Bridson, P. K Cyclic homologs of xanthines. I. Imidazo[4,5–e][1,4]diazepine–5,8–diones / P. K. Bridson, T. P. Weirich / J. Heterocyclic Chem. – 1988. – Vol. 25, Issue 4. – P. 1179–1182. doi : 10.1002/jhet.5570250426.
  75. Daly, J. W. Imidazodiazepinediones: A New Class of Adenosine Receptor Antagonists / J. W. Daly,I.Hide, P. K. Bridson // J. Med. Chem. – 1990. – Vol. 33, Issue 10. – P. 2818–2821. doi : 10.1021/jm00172a022.
  76. Aoyagi, M. Nucleosides and Nucleotides. 130. The Synthesis of Imidazo[4, 5–e][1, 4]Diazepine Nucleosides From N¹–Substituted Inosines / M. Aoyagi, N. Minakawa, A. Matsuda // Nucleosides, Nucleotides and Nucleic Acids. – 1994. – Vol. 13, Issue 6–7. – P. 1535–1549. doi : 10.1080/15257779408012169.
  77. Нosmane, R. S. Models for “Fat” Nucleosides and Nucleotides: Syntheses of “Fat” Xanthine (fX), “Fat” Guanine (fG), and “Fat” Hypoxanthene (fHx) Analogues of the imidazo[4,5–e][1,4]diazepine system / R. S.Hosmane, A. Bhan, M. E. Rauser // Heterocycles. – 1986. – Vol. 24, Issue 10. – P. 2743. doi : 10.3987/r–1986–10–2743.
  78. Нosmane, R. S. The synthesis of ring–expanded analogues of xanthine containing the imidazo[4,5–e][1,4]diazepine ring system / R. S.Hosmane, A. Bhan // J. Heterocycl. Chem. – 1990. – Vol. 27, Issue 7. – P. 2189–2196. doi : 10.1002/jhet.5570270759.
  79. Нosmane, R. S. The Synthesis and Biophysical Investigations of Novel Ring–Expanded Nucleosides, Nucleotides, and Homopolymers Containing the 5:7–Fused Heterocyclic Ring System Imidazo[4,5–e][l,4]diazepine / R. S. Нosmane, A. Bhan, R. L. Karpel // J. Org. Chem. – 1990. – Vol. 55, Issue 23. – P. 5882–5890. doi : 10.1021/jo00310a021.
  80. Ivanov, E. I. Methylation of the cyclic homolog of xanthine / E. I. Ivanov // Chem Heterocycl. Compd. – 1998. – Vol. 34, Issue 5. – P. 620–622. doi : 10.1007/bf02290949.
  81. Синтез и некоторые структурные характеристики гомологов кофеина и изо–кофеина / Э. И. Иванов, Ю. Е. Шапиро, Г. Д. Калаянов и др. // Химия гетероцикл. соедин. – 1992. – № 3. – P. 385–388.
  82. Иванов Э. И. Синтез галогензамещенных имидазоло[4,5–e][1,4]диазепин–5,8–дионов циклических гомологов метилированных ксантинов / Э. И. Иванов, Г. Д. Калаянов, И. М. Ярощенко // Химия гетероцикл. соедин. – 1992. – № 7. – P. 955–958.
  83. Синтез и молекулярная структура 1,4–диметил–4,5,7,8–тетрагидро–6Н–имидазоло[4,5–e][1,4]диазепин–5,8–дитиона / Э. И. Иванов, Г. Д. Калаянов, Л. В. Грищук и др. // Журн. сруктурной химии. – 1993. – Т. 3, № 3. – P. 86–90.
  84. Rajappan, V. Synthesis and guanase inhibition studies of a novel ring–expanded purine analogue containing a 5:7–fused, planar, aromatic heterocyclic ring system / V. Rajappan, R. S. Hosmane // Bioorg. Med. Chem. Lett. – 1998. – Vol. 8, Issue 24. – P. 3649–3652. doi : 10.1016/s0960–894x(98)00672–6.
  85. Rajappan, V. P. Analogues of Azepinomycin as Inhibitors of Guanase / V.P. Rajappan, R. S. Hosmane // Nucleosides, Nucleotides and Nucleic Acids. – 1998. – Vol. 17, Issue 7. – P. 1141–1151. doi : 10.1080/07328319808004227.
  86. Rajappan, V. P. Pentafluorophenol: ASuperiorReagent for Condensations in Heterocyclic Chemistry / V. P. Rajappan, R. S. Hosmane // Synthetic Communications. – 1998. – Vol. 28, Issue 4. – P. 753–764. doi : 10.1080/00397919808005949.
  87. Synthesis of Imidazo[4,5–e][1,4]diazepine and Imidazo[4,5–e][1,4]–oxazepine Derivatives Using Caffeidine, a Hydrolysis Product of Caffeine / T. Ohsaki, T. Kuriki, T. Ueda et al. // Chem. Pharm. Bull. – 1986. – Vol. 34, Issue 9. – P. 3573–3587. doi : 10.1248/cpb.34.3573.
  88. Bhan, A. Reactions of ring–expanded xanthines containing the imidazo[4,5–e][1,4]diazepine ring system / A. Bhan, R. S. Hosmane // J. of Heterocyclic Chem. – 1993. – Vol. 30, Issue 5. – P. 1453–1462. doi : 10.1002/jhet.5570300544.
  89. Bhan, A. Novel inhibitors of guanase / A. Bhan, R. S. Hosmane // Tetrahedron Lett. – 1994. – Vol. 37, Issue 37. – P. 6831–6834. doi : 10.1016/0040–4039(94)85016–x.
  90. Bhan, A. Analogues of Azepinomycin as Inhibitors of Guanase / A. Bhan, R. S. Hosmane // Nucleosides, Nucleotides and Nucleic Acids. – 1995. – Vol. 14, Issue 3–5. – P. 455–458. doi : 10.1080/15257779508012405.
  91. A Unique Diaminomalonate Derivatve useful for Building Novel Heterocycles / A. Bhan, R. S. Hosmane, H. Zhang, N. S. Hosmane // Synthetic Communications. – 1995. – Vol. 25, Issue 18. – P. 2723–2737. doi : 10.1080/00397919508011820.
  92. Иванов, Э. И. Cинтез 1,2,3–триазоло[3,4–e][1,4]диазепина / Э. И. Иванов, Г. Д. Калаянов, И. М. Ярошщенко // Журн. орган. химии. – 1989. – Vol. 25, № 9. – Р. 1975–1979.
  93. Dannhardt, G. Hypertensiv wirksame 5–(β–Aminoethyl)aminoisoxazole : Synthese und Prüfung von Isoxazolopyrazinen und Isoxazolodiazepinen / G. Dannhardt, P. Dominiak, S. Laufer // Arch. Pharm. (Weinheim Ger.). – 1991. – Vol. 324, Issue 3. – P. 141–148. doi : 10.1002/ardp.19913240303.
  94. Synthesis of Isothiazolo[4,3–e][1,4]diazepines / R. Nesi, D. Giomi, L. Quartara, S. Papaleo // Gazz. Chim. Ital. – 1990. – Vol. 120. – P. 725–730.
  95. –Phenyl–5–carbomethoxymethylene–5H–isoxazolo[4,5–e][1,4] diazepine–6,8(4H,7H)dione : A New Seven Membered Binuclear System / R. Nesi, D. Giomi, L. Quartara et al. // Heterocyles. – 1987. – Vol. 26, Issue 9. – Р. 2419. doi : 10.3987/r–1987–09–2419.
  96. Synthesis of a Multifunctional Oxazolo[5,4–e][1,4]diazepine Skeleton / G. Kolavi, I. Im, Y. C. Kim, H. Ko // Bull. Korean Chem. Soc. – 2011. – Vol. 32, Issue 3. – Р. 1041–1044. doi : 10.5012/bkcs.2011.32.3.1041.
  97. Synthetic studies in the 1,2–dithiole series. IV. The methylation of 4–Benzamido–1,2–dithiole–3–thione / R. F. C. Brown,I.D. Rae, J. S. Shannon et al. // Australian J. Chem. – 1966. – Vol. 19, Issue 3. – Р. 503. doi : 10.1071/ch9660503.
  98. Synthesis of Isoselenazolo– or Isothiazolo[4,3–e][1,4]diazepines / T. Ueda, Y. Kato, J. Sakakibara, M. Murata // Chem. Pharm. Bull. – 1988. – Vol. 36, Issue 8. – Р. 2902–2908. doi : 10.1248/cpb.36.2902.
  99. Ried, W. Neue Ringsysteme aus heterocyclischen 5–substituierten Tetrazolderivaten / W. Ried, S. Becker // Liebigs Ann. Chem. – 1989. – Vol. 1989, Issue 1. – Р. 83–85. doi : 10.1002/jlac.198919890116.
  100. Shafiee, A. Syntheses of 7–phenyl–5H–thiazolo[5,4–e]pyrrolo[1,2–a][1,4]diazepin–10(9H)–one, 7–phenyl–5H–thiazolo[5,4–e][1,2,3,4]tetrazolo [5,1–c]pyrrolo[1,2–a][1,4]diazepine and 7–phenyl–5H–thiazolo[5,4–e][1,3,4] triazolo[5,1–c]pyrrolo[1,2–a][1,4]diazepines / A. Shafiee, M. Shekarchi // J. Het. Chem. – 2002. – Vol. 39, Issue 1. – Р. 213–216. doi : 10.1002/jhet.5570390130.

Downloads

Published

2017-03-23

How to Cite

(1)
Kemskii, S. V.; Bolbut, A. V.; Dmytriv, Y. V.; Vovk, M. V. Azolo[1,4]diazepines: The Methods of Synthesis and Structural Modification. J. Org. Pharm. Chem. 2017, 15, 3-27.

Issue

Vol. 15 No. 1(57) (2017)

Section

Original Researches

License

Copyright (c) 2017 National University of Pharmacy

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Authors publishing their works in the Journal of Organic and Pharmaceutical Chemistry agree with the following terms:

1. Authors retain copyright and grant the journal the right of the first publication of the work under Creative Commons Attribution License allowing everyone to distribute and re-use the published material if proper citation of the original publication is given.

2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal’s published version of the work (e.g., post it to an institutional repository or publish it in a book) providing proper citation of the original publication.

3. Authors are permitted and encouraged to post their work online (e.g. in institutional repositories or on authors’ personal websites) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (see The Effect of Open Access).