The synthesis and antimicrobial activity of 5-aroxy-2,6-dihydro-1H-pyrrolo[3,4-d] pyridazine-1-ones

Authors

  • A. M. Grozav Bukovinian State Medical University, Ukraine https://orcid.org/0000-0001-9821-0695
  • M. Z. Fedoriv Ivano-Frankivsk National Medical University, Ukraine
  • V. O. Chornous Bukovinian State Medical University, Ukraine
  • N. D. Yakovychuk Bukovinian State Medical University, Ukraine
  • S. Ye. Deineka Bukovinian State Medical University, Ukraine
  • S. V. Kemskyi Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.19.970

Keywords:

polyfunctional pyrroles, hydrazine hydrate, pyridazinoanelination, 1H-pyrrolo[3, 4-d]pyridazine-1-one, antimicrobial activity

Abstract

Aim. To develop an effective method for the synthesis of 5-aroxy-2,6-dihydro-1Н-pyrrolo[3,4-d]pyridazine-1-ones as promising objects to be investigated in the context of their antimicrobial activity.
Results and discussion. It has been found that ethyl 4-formyl-5-chloro-1Н-pyrrole-3-carboxylates can be used as convenient source substrates for building 5-aroxy-2,6-dihydro-1Н-pyrrolo[3,4-d]pyridazine-1-one systems. MBsC (MFsC) and MBcC (MFcC) of the pyrrolo[3,4-d]pyridazine-1-ones synthesized were within the range
of 31.25-125 μg/ml.
Experimental part. The two-stage synthesis of 5-aroxy-2,6-dihydro-1Н-pyrrolo[3,4-d]pyridazine-1-ones was performed. The chemical composition and the structure of the compounds synthesized were confirmed by chromatography-mass spectra, IR- and NMR 1Н (13С) spectra. The screening of the antimicrobial activity using the micromethod of the double series dilutions in the liquid nutrient medium allowed identifying compounds with a moderate activity.
Conclusions. A preparative convenient synthesis of 5-aroxy-2,6-dihydro-1Н-pyrrolo[3,4-d]pyridazine-1-ones has been developed. This method assumes the nucleophilic substitution of the chlorine atom in ethyl 4-formyl-5-chloro-1Н-pyrrole-3-carboxilates with an aroxyl fragment followed by the subsequent pyridazinoanelination of
ethyl 5-aroxy-4-formyl-1Н-pyrrole-3-carboxylates by hydrazine hydrate. The results of the antimicrobial activity of the substances synthesized substantiate the feasibility of further in-depth studies in this area.

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Published

2019-06-14

How to Cite

(1)
Grozav, A. M.; Fedoriv, M. Z.; Chornous, V. O.; Yakovychuk, N. D.; Deineka, S. Y.; Kemskyi, S. V. The Synthesis and Antimicrobial Activity of 5-Aroxy-2,6-Dihydro-1H-pyrrolo[3,4-D] Pyridazine-1-Ones. J. Org. Pharm. Chem. 2019, 17, 11-16.

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Original Researches