Abstract
A series of thieno[2,3-b]thiophene moiety-containing bis-cyanopyrazoles 5a–c, bis-aminopyrazole 9 and bis-pyridazine derivatives 11 were synthesized and evaluated in vitro for their antimicrobial potential. The antimicrobial activity of some selected products was evaluated and showed good results. 5,5'-(3,4-Dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(3-acetyl-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile) (5d) was found to be more potent than the standard drug amphotericin B against Geotricum candidum and equipotent to amphotericin Bagainst Syncephalastrum racemosum. In addition, it was found to be equipotent to the standard drug Penicillin G against Staphylococcus aureus. Moreover, it was more potent than the standard drug streptomycin against Pseudomonas aeruginosa and Escherichia coli.
Highlights
Thieno[2,3-b]thiophenes possess important biological activities, including antiinflammatory [1,2], antimicrobial [3], analgesic [4] properties, antiproliferative activity [5], antagonism of α1 adrenoceptors [6] and prevention of cartilage destruction in articular diseases [7], In addition, thieno[2,3-b]thiophenes have shown useful reactivity as co-polymerization agents [8] and as semiconductors [9]
Pyridazine compounds are commonly used as anticancer [12], antituberculosis [13], antihypertensive [14], antifungal [15,16], or antimicrobial [17,18,19,20] agents, due to their intense biological activity
Encouraged by all these findings and in continuation of our ongoing research program investigating the utilisation of 3,3'-(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(3-oxopropanenitrile) (1) as a versatile and useful building block for the synthesis of a wide variety of bis-heterocyclic systems [21,22,23,24,25], we report in the present work an efficient and rapid method for the synthesis of a series of bis-cyanopyrazole, bis-aminopyrazole and bis-pyridazine derivatives containing thieno[2,3-b]thiophene as a base unit
Summary
Thieno[2,3-b]thiophenes possess important biological activities, including antiinflammatory [1,2], antimicrobial [3], analgesic [4] properties, antiproliferative activity [5], antagonism of α1 adrenoceptors [6] and prevention of cartilage destruction in articular diseases [7], In addition, thieno[2,3-b]thiophenes have shown useful reactivity as co-polymerization agents [8] and as semiconductors [9]. Pyridazine compounds are commonly used as anticancer [12], antituberculosis [13], antihypertensive [14], antifungal [15,16], or antimicrobial [17,18,19,20] agents, due to their intense biological activity. Encouraged by all these findings and in continuation of our ongoing research program investigating the utilisation of 3,3'-(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(3-oxopropanenitrile) (1) as a versatile and useful building block for the synthesis of a wide variety of bis-heterocyclic systems [21,22,23,24,25], we report in the present work an efficient and rapid method for the synthesis of a series of bis-cyanopyrazole, bis-aminopyrazole and bis-pyridazine derivatives containing thieno[2,3-b]thiophene as a base unit
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