Synthesis and Antimicrobial Evaluation of Some New Thiophene Derivatives

Khalil, A. M.; Berghot, M. A.; El‐Ghani, Ghada E. Abd; Gouda, Moustafa A.

doi:10.1080/00397910903161652

Cited by 20 publications

(19 citation statements)

References 14 publications

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“…The start robenzo[b]thiophene-3-carboxam n of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1) [10], with 3-(3,4-dimethyl-1H-pyrazol-1-yl)-3-oxopropanenitrile (2) [11] through modification of the previously reported method for the synthesis of analogues [11,12]. Also, N-phenylthiazolone derivatives 6 and 8 were prepared according to the methods reported in literature [9]. Coupling of compounds 3 and 6 with various aryldiazon ides 4a-e and 2-(4-(arylhydrazono)-5-oxo-3-phenylthiazolidin-2-ylidene)-3-cyanoacetamides 7a-e, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The dyeing assessment, fastness tests, colour measurements were carried out in El-Nasr Company for Spinning and Weaving El-Mahalla El-Kubra, Egypt. Thiophene derivatives 6, 7b and 8 were prepared according to the previously reported methods [9].…”

Section: Methodsmentioning

confidence: 99%

“…A square of whi fab The sam by stitching pieces of dyed polyester fabric be ed polyester, all of equal diameters and then tre polyester on a Xenotest l Hanau, chamber temperature 25-30 o C, black panel tem ative humidity 50-60%, and dark glass (UV) filter sys tristi he colour parameters of the dyed fabrics were determi channel photodetector (model MCPD1110A), equipped wi ted to obtain the target compounds are de ing 2-(2-cyanoacetylamino)-4,5,6,7-tetrahyd ide 3 [9] was obtained via cyanoacetylatio ium chlorides in pyridine afforded 2-(arylhydrazono)-3-cyanoacetam = 3411-ric back and forth twenty times by making ten complete turns of the crank. For wet rubbing test, the testing square was thoroughly wet in distilled water.…”

Section: ) Fastness To Rubbingmentioning

confidence: 99%

“…In recent years, efforts have been made to replace certain anthraquinone dyes with technically equivalent azo dyes for both the environmental and economic reasons [6]. In view of the above-mentioned findings and as continuation of our efforts [7,8] to identify new candidates that may be of value in designing new azo-dispersed dyes, we report herein the synthesis of some new azo-dispersed dyes derived from 2-(2-cyanoacetamido)-4,5,6,7-tetrahydrobenzo [b]thiophene-3-carboxamide [9].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Azo-Dispersed Dyes Derived From 2-(2-Cyanoacetamido)-4,5,6,7-Tetrahydrobenzo-[b]Thiophene-3-Carboxamid]

Gouda¹,

Eldien²,

Girges³

et al. 2011

Latvian Journal of Chemistry

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Coupling of 2-(2-cyanoacetylamino) -4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (3) or 2-[2-(5-oxo-3-phenylthiazolidin-2-ylidene)]-2-cyanoacetamido-4,5,7-tetrahydrobenzo[b]thiophene-3-carboximide (6) with various diazotized aryl amines in pyridine gave the corresponding aryl hydrazonopropionitrile derivatives. Some of the synthesized dyes were applied to polyester fabrics as dispersed dyes in which their colour measurements and fastness properties were evaluated.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: ) Fastness To Rubbingmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Azo-Dispersed Dyes Derived From 2-(2-Cyanoacetamido)-4,5,6,7-Tetrahydrobenzo-[b]Thiophene-3-Carboxamid]

Gouda¹,

Eldien²,

Girges³

et al. 2011

Latvian Journal of Chemistry

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“…5) On the other side, the derivatives of tetrahydrobenzo [b] thiophene exist in many pharmaceutical applications such as anti-tumor, 6) antimicrobial, [7][8][9] antiviral, 10) anti-leishmanial agents, 11) antioxidant activity, 12) anti-arrhythmic, serotonin antagonist and anti-anxiety activities. 13) Recently we were involved through the synthesis of polyfunctional heterocyclic compounds, where the 2-cyanomethylbenzo[c] imidazole was used as the key starting compound.…”

mentioning

confidence: 99%

Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[<i>b</i>]thiophene Together with Their Cytotoxic Evaluations

Abdallah

Mohareb

Khalil

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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The 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene was the key starting compound used to synthesize new thiazole, pyrimidine, pyran, pyridine and thiazine derivatives. The cytotoxicity of the synthesized compounds was studied towards the three cancer cell lines namely MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (central nervous system (CNS) cancer) in addition to the normal cell line (WI-38) using doxorubicin as the reference drug. The study showed that compounds 5, 9a, 15b, 17c, 18 and 21b were the most potent compounds. anti-leishmanial agents, 11) antioxidant activity, 12) anti-arrhythmic, serotonin antagonist and anti-anxiety activities. Key words 13)Recently we were involved through the synthesis of polyfunctional heterocyclic compounds, where the 2-cyanomethylbenzo[c] imidazole was used as the key starting compound.14) In addition, we were involved through the reaction of ethyl acetoacetate with elemental sulphur and either malononitrile or ethyl cyanoacetate gave thiophene derivatives. 15) In the present work we were concerned through exploring the reactivity of the amino group present in the 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b] thiophene 16) towards different chemical reagents to afford a vast number of heterocyclic compounds involving tetrahydrobenzo[b]-thiophene moiety and evaluating their cytotoxicity. Results and DiscussionChemistry The reaction of the 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b] thiophene with triethyl orthoformate in acetic acid gave the ethyl N- (3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl) formimidate 1. The analytical and spectral data of compound 1 were the tools of its structural elucidation. Compound 1 reacted with aniline to give the N-phenyl formamidine derivative 2. The elemental and spectral data of compound 2 were consistent with its proposed structure. Thus, 1 H-NMR spectrum of compound 2 showed, beside the expected signals, a singlet at 6.95 ppm δ for CH moiety, a muliplet at δ 7.27-7.90 ppm for phenyl ring and a singlet at δ 8.36 ppm for NH group. On the other hand, the reaction of compound 1 with malononitrile gave the imino-methyl malononitrile derivative 3. The analytical and spectral data of compound 3 were in agreement with its structure (see Experimental section). The reaction of compound 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b] thiophene with phenylisothiocyanate and chloroacetone gave the thiazole derivative 5. Formation of the latter product took place through the intermediate formation of 4 followed by water elimination (Chart 1).Next we studied the possibility of compound 2-amino-3-cyano-4, 5,6,7-tetrahydrobenzo[b] thiophene to form thiourea derivative. Thus, compound 2-amino-3-cyano-4, 5,6,7-tetrahydrobenzo[b] thiophene reacted with phenyl

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Synthesis, Characterization, Antioxidant and Antitumor Evaluation of Some New Thiazolidine and Thiazolidinone Derivatives

Gouda

Abu‐Hashem

2010

Archiv der Pharmazie

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2-(2-Cyano-acetylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid ethyl ester (2) was utilized as a key intermediate for the synthesis of thiocarbamoyl derivative 3 via its reaction with phenyl isothiocyanate. Treatment of 3 with chloroacetyl chloride afforded thiazolidin-5-one 4. Compound 7 reacted with different α-halo carbonyl compounds to give thiazolidine 8a,b, and thiazolidin-4-one derivatives 9. Treatment of 4 with the appropriate aromatic aldehyde and tolyl diazonium chloride afforded the corresponding thiazolidin-5-one derivatives 5a,b and 6, respectively. The thiazolidin-4-one derivative 10 was obtained via the reaction of compound 2 with 2-mercaptoacetic acid. Finally, the thiazoline 11 was obtained via the reaction of compound 2 with phenyl isothiocyanate/sulfur. The title compounds were characterized by elemental analyses and spectral data. The quantum mechanical calculations for some compounds were accomplished and subjected for antioxidant and antitumor studies, whereas, some of them exhibited promising activities.

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Synthesis and Antimicrobial Evaluation of Some New Thiophene Derivatives

Cited by 20 publications

References 14 publications

Synthesis of Azo-Dispersed Dyes Derived From 2-(2-Cyanoacetamido)-4,5,6,7-Tetrahydrobenzo-[b]Thiophene-3-Carboxamid]

Synthesis of Azo-Dispersed Dyes Derived From 2-(2-Cyanoacetamido)-4,5,6,7-Tetrahydrobenzo-[b]Thiophene-3-Carboxamid]

Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[<i>b</i>]thiophene Together with Their Cytotoxic Evaluations

Synthesis, Characterization, Antioxidant and Antitumor Evaluation of Some New Thiazolidine and Thiazolidinone Derivatives

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