Studies of Thiazolopyridines, Part 6: Synthesis and Antimicrobial Evaluation of Some Novel Thiazolo[3,2-a] Pyridine and Thiazolo[2′,3′:6,1]-pyrido[2,3-d]pyrimidine Derivatives

Ali, Gameel A. M. El‐Hag; Khalil, A. M.; Lamphon, R. Q.; El‐Maghraby, A. A.

doi:10.1080/104265090889620

Cited by 25 publications

(9 citation statements)

References 4 publications

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“…Literature review has disclosed that thiazoles in combination with coumarin ring in their core structure as a hybrid scaffold have unveiled significant pharmacological activities such as anticonvulsant [20], antimicrobial [21], anti-inflammatory [22], anti-tumor [23], antioxidant [24], etc. Also, thiazolo [3,2-a]pyridines with two or more fused heterocyclic rings in their structure have prominent diverse bioactivities such as CDK2-cyclin-A inhibitor [25], α-glucosidase inhibitor [26], uterus stimulant [27], and antimicrobial activities [28].…”

Section: Introductionmentioning

confidence: 99%

An Efficient One‐pot Three‐component Method for the Synthesis of 5‐Amino‐3‐(2‐oxo‐2H‐chromen‐3‐yl)‐7‐aryl‐7H‐thiazolo[3,2‐a]pyridine‐6,8‐dicarbonitriles

Kavitha

Srikrishna

Dubey

et al. 2019

Journal of Heterocyclic Chem

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A facile, convenient, and adequate method has been developed for the synthesis of novel 5‐amino‐3‐(2‐oxo‐2H‐chromen‐3‐yl)‐7‐aryl‐7H‐thiazolo[3,2‐a]pyridine‐6,8‐dicarbonitriles (6) by employing 2‐(4‐(2‐oxo‐2H‐chromen‐3‐yl)thiazol‐2‐yl)acetonitrile (3) as an important precursor. Initially, we have synthesized the target compounds in a stepwise manner and then approached a tandem method to examine the feasibility of one‐pot method. Subsequently, one‐pot three‐component protocol has been established for the synthesis of title compounds by the reaction of 3 with benzaldehyde and malononitrile in refluxing ethanol engender a new six‐membered thiazolo[3,2‐a] pyridine as a hybrid scaffold. Reaction conditions were optimized for this reaction and a broad substrate scope with various aryl and heteroaryl aldehydes make this protocol very practical, attractive, and worthy. Mechanistic aspects for the formation of these compounds were outlined comprehensively. Characterization of these newly synthesized compounds was achieved by means of IR, 1H NMR, 13C NMR, and HRMS.

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Section: Introductionmentioning

confidence: 99%

An Efficient One‐pot Three‐component Method for the Synthesis of 5‐Amino‐3‐(2‐oxo‐2H‐chromen‐3‐yl)‐7‐aryl‐7H‐thiazolo[3,2‐a]pyridine‐6,8‐dicarbonitriles

Kavitha

Srikrishna

Dubey

et al. 2019

Journal of Heterocyclic Chem

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“…It is thought of interest to accommodate thiazolidin-4-one and pyridine moiety in a single molecular framework. With this in mind and in continuation of our research on synthesis of biologically active antimicrobial heterocylcles [22][23][24][25][26][27][28][29][30] we are report here synthesis of some a novel series of thiazolidinones class having pyridine moiety in addition to investigation of their antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial Evaluation of Some Hitherto Unknown 4-Oxo-Thiazoles and Thiazolo [3, 2-A] Pyridines

Shedid

Ali

2018

Al-Azhar Bulletin of Science

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2-(4-Oxothiazolidin-2-ylidene) acetonitrile and ethyl-2-(4-oxothiazolidin-2-ylidene) acetate (1a, b), were condensed with anthralaldehyde (1:1 molar ratio) and gave 4, 5-dihydro-4-oxothiazole derivatives (2a, b). Refluxing of 2-(Antharacene-9-yl-methylene) malononitrile in acetic acid with thioglycollic acid gave (3). 4-Thiazolidinones containing bis aryl methylidine moieties (4a-c) and (5a, b) were produced via condensation of either (2a) or (3) with different aromatic aldehydes (1:1 molar ratio). Heating of (2a) with α-substituted cin-namonitriles gave the expected substituted thiazolo [3, 2-a] pyridines (6a-d), (8) and (10a-c). The synthesized compounds have been screened for their antimicrobial activities against some selected species of Gram-positive (G +). Gram-negative (G-) bacteria and 3 different types of fungi. They were found to be more active against Gram positive than Gram negative bacteria.

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“…Thiazolo[3,2‐ a ]pyridine derivatives are found to exhibit a broad spectrum of potent anticancer activity and are useful for chemotherapy of various cancers, such as leukemia, lung cancer, and melanoma . Also thiazolo[3,2‐ a ]pyridines have many important bioactivities such as beta‐amyloid production inhibitor , potent CDK2‐cyclin A inhibitor , potential uterus stimulant , coronary dilator, antihypertensive, muscle relaxant , antibacterial, and antifungal . These derivatives have been found to scavenge free radicals .…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Green Synthesis of Thiazolo[3,2‐a]pyridine Derivatives via Tandem Cyclization in Aqueous Media

Boominathan

Nagaraj

Maheshwaran

et al. 2013

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Facile, three-component domino reactions of readily available thioglycolic acid/ethyl thioglycolate, aromatic aldehydes, and malononitrile/ethyl cyanoacetate in aqueous potassium carbonate at room temperature afforded thiazolo[3,2-a]pyridine derivatives chemoselectively in good to excellent yield. All the formed 4H-chromenes were characterized by spectral and X-ray methods.

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Studies of Thiazolopyridines, Part 6: Synthesis and Antimicrobial Evaluation of Some Novel Thiazolo[3,2-a] Pyridine and Thiazolo[2′,3′:6,1]-pyrido[2,3-d]pyrimidine Derivatives

Cited by 25 publications

References 4 publications

An Efficient One‐pot Three‐component Method for the Synthesis of 5‐Amino‐3‐(2‐oxo‐2H‐chromen‐3‐yl)‐7‐aryl‐7H‐thiazolo[3,2‐a]pyridine‐6,8‐dicarbonitriles

An Efficient One‐pot Three‐component Method for the Synthesis of 5‐Amino‐3‐(2‐oxo‐2H‐chromen‐3‐yl)‐7‐aryl‐7H‐thiazolo[3,2‐a]pyridine‐6,8‐dicarbonitriles

Synthesis, Characterization and Antimicrobial Evaluation of Some Hitherto Unknown 4-Oxo-Thiazoles and Thiazolo [3, 2-A] Pyridines

One‐Pot Green Synthesis of Thiazolo[3,2‐a]pyridine Derivatives via Tandem Cyclization in Aqueous Media

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