Novel quinazolinone derivatives: synthesis and antimicrobial activity

Self Cite

In this effort, 2‐aminothiophene‐3‐carboxylate (1) was prepared using Gewald's methodology. This 2‐aminothiophene derivative was diazotized and coupled with malononitrile to obtain the nitrile derivative (2), which was utilized as key synthon for the synthesis of polyfunctionally substituted heterocycles via its reactions with some nitrogen and carbon nucleophiles. On the other hand, a facile and convenient syntheses of thiazolidinone, pyrrolidinone, and chromene derivatives incorporating thiophene moiety via the versatile, readily accessible 2‐aminothiophene‐3‐carboxylate (1) were also described.

Section: Resultsmentioning

confidence: 99%

Efficient Syntheses of Some New Thiophene‐Based Heterocycles

El‐Mekabaty

Habib

Moawad

et al. 2016

Self Cite

“…Quinazoline and its derivatives have emerged as an important class of nitrogen‐containing heterocycles that have attracted significant synthetic interest because of their pharmacological and therapeutic properties such as antitumor, antibacterial, antifungal, antihypertension, antitubercular, antioxidant, anticonvulsant, anticancer, anti‐inflammatory, and antihyperlipidemic activities . Some heterocyclic compounds containing quinazoline ring system also showed to be potent inhibitors of thymidylate synthase.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitumor activities of novel bis‐quinazolin‐4(3H)‐ones

Rahmannejadi

Yavari

Khabnadideh

2020

With the aim of obtaining new antitumor agents, a series of bis‐quinazolin‐4(3H)‐ones (3a‐3 f) were designed and synthesized. These products contain 4‐oxo‐1,2,3,4‐tetrahydro‐quinazoline and 3H‐quinazolin‐4‐one moieties linked together via a propyl chain. Cytotoxic activities of 3a‐3 f were evaluated against lung adenocarcinoma (A549), breast carcinoma (MCF‐7) and ovarian cancer (SKOV3) cell lines using MTT method. Cisplatin was used as a positive control. Among the tested compounds 3a, 3b, and 3e showed the best cytotoxic activities against all cancerous cell lines with IC50 values even less than cisplatin. Compounds 3d and 3f also showed desirable cytotoxic activities especially against A549 and MCF‐7.

“…We have recently reviewed the methods of preparation and the chemical reactivity of 3‐cyanoacetylindole as building block for the synthesis of polyfunctionalized 3‐substituted indole derivatives with pharmacological interest . As a consequence of our recent work aimed at synthesis of new heterocyclic systems with remarkable biological importance , it was planned to present an efficient regioselective synthesis of some novel biologically active heterocycles such as pyrazolo[1,5‐ a ]pyrimidines, imidazo[1,2‐ b ]pyrazoles, pyrazolo[1,5‐ a ][1,3]diazepine and pyrazolo[1,5‐ c ][1,3,5]thiadiazine bearing indole ring system, which have not been reported hitherto. The results of screening of their biological activity will be reported in due course.…”

Section: Introductionmentioning

confidence: 99%

An Efficient and Facile Synthesis of Functionalized Indole‐3‐yl Pyrazole Derivatives Starting from 3‐Cyanoacetylindole

El‐Mekabaty

Mesbah

Fadda

2016

Self Cite

The versatile hitherto reported 3‐(1H‐indol‐3‐yl)‐1H‐pyrazol‐5‐amine (4) was synthesized by the reaction of 3‐cyanoacetylindole (3) with hydrazine hydrate in refluxing ethanol and used as a key intermediate for the synthesis of novel pyrazolo[1,5‐a]pyrimidines via its reactions with appropriate 1,3‐biselectrophilic reagents or through three‐component condensations with triethyl orthoformate and compounds possessing an activated methylene group. Besides, the applicability and synthetic potency of (4) to attain polyfunctionally substituted imidazo[1,2‐b]pyrazole, pyrazolo[1,5‐a][1,3]diazepine and pyrazolo[1,5‐c][1,3,5]thiadiazine derivatives of an expected pharmaceutical interest have been investigated. The mechanistic aspects for the formation of the newly synthesized compounds are discussed.