Reactions of Benzoyl Isothiocyanate with Active Methylene Reagents: A Novel Synthesis of Thiophene, Thiazoline and Thieno[2,3‐<i>d</i>]Pyrimidine Derivatives

Mohareb, Rafat M.; Aziz, Suzan Ibrahim; Saved, Nadia Iskander Abdel; Shams, H. Z.

doi:10.1002/jccs.199200030

Cited by 17 publications

(8 citation statements)

References 6 publications

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“…The synthesis of several heteroaromatic coumarinyl derivatives from haloacetyl-and halocoumarins is reported in the literature [233][234][235][236]. In order to look for new phosphorous-containing coumarin derivatives, with potential biological activities, the synthesis of new coumarin phosphonates and phosphates was developed.…”

Section: From Alkylcoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

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Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

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Section: From Alkylcoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

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“…In the present work, we are demonstrating the synthesis of thiophene derivatives together with their cytotoxic evaluation, in continuation of our interest in the design of bioactive heterocycles (23)(24)(25)(26)(27). Thus, the reaction of ethyl acetoacetate with elemental sulphur and either malononitrile or ethyl cyanoacetate gave the thiophene derivatives 1a,b, respectively.…”

Section: Chemistrymentioning

confidence: 75%

Synthesis and structure elucidation of some novel thiophene and benzothiophene derivatives as cytotoxic agents

et al. 2016

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Synthesis and structure elucidation of some novel thiophene and benzothiophene derivatives as cytotoxic agentsAtt empting to produce cyclized systems with potential anti-proliferative activity, a series of novel thiophene and benzothiophene derivatives were designed and synthesized. The reactivity of the latt er derivatives towards diff erent chemical reagents was studied. Twenty-one compounds were synthesized and evaluated as anti-cancer agents. The results showed that ethyl 5-amino-3-(4-chlorostyryl)-4-cyanothiophene-2-carboxylate (5b), ethyl 5-amino-4-((4-methoxyphenyl)carbonyl)-3-methylhiophene-2-carboxylate (8c) and 5-3-(ethoxy-3-oxopropanamido)-3-methyl-4-(phenylcarbamoyl)thiophene-2-carboxylate (9) were the most active compounds towards three tumor cell lines -MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) and a normal fi broblast human cell line (WI-38) compared to the anti-proliferative eff ects of the reference control doxorubicin.

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“…At the other extreme, the reaction of the start precursor 4 with phenyl isothiocyanate in basic dimethylformamide followed by heterocyclization using α-halo carbonyl reagents (XCH 2 -C(=O)R; X=Cl, R=CO 2 Et; X=Br, R=Ph; X=Cl, R=CH 3 ) afforded the polyfunctional thiophene or thiazole derivatives 18a-b, 19 , respectively ( Scheme 7 ). The reaction product depended on the nature of the α-halocarbonyl reagent [ 44 ]. The mechanism of reaction involved the intermediate formation of the potassium sulphide salt A.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems

et al. 2011

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A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone) counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, 2-ethoxycarbonyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide or 2-phenylcarbamoyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide systems as precursors. The latter compounds were used to synthesize polyfunctional thiophene-, thiazole-, pyrazole, pyridine-, pyrimidine-, oxazine-, as well as acyclic moieties. The dyes and dye precursors were characterized by elemental analysis and spectral methods. All dyes and their precursors were screened in vitro and evaluated for both their antibacterial and antifungal activities. MIC data of the novel dye systems and their respective precursors showed significant antimicrobial activity against most tested organisms. Some compounds exhibited comparable or even higher efficiency than selected standards. Dyes were applied at 5% depth for disperse dyeing of nylon, acetate and polyester fabrics. Their spectral characteristics and fastness properties were measured and evaluated.

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Reactions of Benzoyl Isothiocyanate with Active Methylene Reagents: A Novel Synthesis of Thiophene, Thiazoline and Thieno[2,3‐d]Pyrimidine Derivatives

Cited by 17 publications

References 6 publications

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Synthesis and structure elucidation of some novel thiophene and benzothiophene derivatives as cytotoxic agents

Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems

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