The Reaction of 2-Amino-4,5,6,7-tetrahydrobenzo[&amp;lt;i&amp;gt;b&amp;lt;/i&amp;gt;]thiophenes with Benzoyl-Isothiocyanate: Synthesis of Annulated Thiophene Derivatives and Their Antitumor Evaluations

El-Sharkawy, Karam Ahmed; El‐Sehrawi, Hend M.; Ibrahim, Rehab Ali

doi:10.4236/ijoc.2012.22020

Cited by 18 publications

(9 citation statements)

References 20 publications

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“…Sharkawy et al [31] synthesized a series of thiophene incorporating pyrazolone moieties via diazo coupling of diazonium salt of 3-substituted-2-amino-4,5,6,7-tetrahydrobenzo[ b ]thiophenes with 3-methyl-1 H -pyrazol-5(4 H )-one, 3-methyl-1-phenyl-1 H -pyrazol-5(4 H )-one or 3-amino-1 H -pyrazol-5(4 H )-one, respectively as represented in Scheme 15. Newly synthesized derivatives were tested for cytotoxicity against the well known established model ehrlich ascites carcinoma cells (EAC) in vitro.…”

Section: Introductionmentioning

confidence: 99%

Therapeutic importance of synthetic thiophene

Shah

Verma

2018

Chemistry Central Journal

177

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Thiophene and its substituted derivatives are very important class of heterocyclic compounds which shows interesting applications in the field of medicinal chemistry. It has made an indispensable anchor for medicinal chemists to produce combinatorial library and carry out exhaustive efforts in the search of lead molecules. It has been reported to possess a wide range of therapeutic properties with diverse applications in medicinal chemistry and material science, attracting great interest in industry as well as academia. It has been proven to be effectual drugs in present respective disease scenario. They are remarkably effective compounds both with respect to their biological and physiological functions such as anti-inflammatory, anti-psychotic, anti-arrhythmic, anti-anxiety, anti-fungal, antioxidant, estrogen receptor modulating, anti-mitotic, anti-microbial, kinases inhibiting and anti-cancer. Thus the synthesis and characterization of novel thiophene moieties with wider therapeutic activity is a topic of interest for the medicinal chemist to synthesize and investigate new structural prototypes with more effective pharmacological activity. However, several commercially available drugs such as Tipepidine, Tiquizium Bromides, Timepidium Bromide, Dorzolamide, Tioconazole, Citizolam, Sertaconazole Nitrate and Benocyclidine also contain thiophene nucleus. Therefore, it seems to be a requirement to collect recent information in order to understand the current status of the thiophene nucleus in medicinal chemistry research.

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Section: Introductionmentioning

confidence: 99%

Therapeutic importance of synthetic thiophene

Shah

Verma

2018

Chemistry Central Journal

177

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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.…”

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Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[b]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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“…11) Triazoles, in particular, substituted 1,2,4-triazoles are among the various heterocycles that have received the most attention during the last decades as potential antimicrobial agents. [12][13][14] In spite of a large number of antibiotics and chemotherapeutics available for medical usage, the increasing demands make it necessary to continue the search for new antimicrobial substances. Though, various molecules were designed and synthesized for this aim, the efforts have demonstrated that 1,3-diazines and 1,2,4-triazoles could be considered as possible antimicrobial agents.…”

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confidence: 99%

“…The change of its carboxyl group to an amide group increased its bacteriostatic effects. 26,27) In the present investigation the authors synthesizes ethyl 2-(3-dodecanoylthioureido)-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylate 3 from the reaction of lauroyl isothiocyanate 15,28) with o-aminoester derivative 13) as starting material. Compound 3 is utilized as a novel building block to give the target condensed 1,3-diazines and 1,3-thiazines via intramolecular exo-trig annulations as well as some 1,2,4-triazole derivatives bearing lauryl group hoping to increase their antimicrobial properties.…”

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confidence: 99%