Convenient synthesis and antitumor evaluation of some new 9-ethyl-3-(hetaryl)carbazoles

Bondock, Samir; Alqahtani, Salwa; Fouda, Ahmed M.

doi:10.1080/00397911.2019.1616759

Cited by 12 publications

(6 citation statements)

References 40 publications

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“…The commencing material, N-(9-ethylcarbazol-3-yl)-2-cyanoacetamide (1), was obtained as previously described by us via the cyanoacetylation of 3-amino-9-ethylcarbazole with a mixture of cyanoacetic acid and acetic anhydride under hot condition. [34] It has been reported that the base catalyzed nucleophilic addition reaction of the active methylene reagents to isothiocyanates produced thiocarbamoyl derivatives which could be easily cyclized with α-halo carbonyl reagents to afford either thiazole, thiophene, and/or 1,3,4-thiadiazole derivatives. [37,38] In this line, the behavior of acetamide 1 towards phenyl isothiocyanate and α-halo carbonyl compounds were investigated.…”

Section: Resultsmentioning

confidence: 99%

“…[31] Molecular hybridization approached of two or more bioactive units in one molecule was documented to be effective tool in the construction of innovative drugs with promising pharmacophoric properties. [32] In the light of these facts and in continuation of our interest in the construction of bioactive carbazole derivatives, [33,34] we present here the synthesis and in vitro antitumor evaluation of certain novel carbazole-based thiazole, thiophene, and 1,3,4-thiadiazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and In Vitro Antitumor Evaluation of Some Carbazole‐Based Thiazole, Thiophene, and 1,3,4‐Thiadiazole Derivatives

2020

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In continuation to our efforts to discover new powerful antitumor agents, a series of new carbazole-based thiazole, thiophene, and 1,3,4-thiadiazole derivatives were conveniently synthesized, spectrally characterized, and mechanistically discussed. The synthetic strategy involves the cyclization reactions of two easily attainable commencing materials, N-(9-ethylcarbazol-3-yl)-2-cyanoacetamide (1) and 2-((9-ethylcarbazol-3yl)hydrazono)-3-oxo-N-phenylbutanethioamide (20), with αchlorocarbonyl reagents, α-chloronitrile, and hydrazonoyl chlorides in a basic medium. They were also assessed against three human tumor cell lines (HCT-116, HepG-2, and MCF-7) and one non-tumor human cell line (REP1) for their in vitro antitumor activity. The results demonstrated that seven carbazoles 4, 15 a, 15 b, 15 d, 20, 22 b, and 29 a had high antitumor activity, having IC 50 values in the range 5.24-9.70 μM. The most potent carbazoles 15 b, 20 and 22 b inhibited the growth of all tested tumor cell lines and did not display human toxicity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and In Vitro Antitumor Evaluation of Some Carbazole‐Based Thiazole, Thiophene, and 1,3,4‐Thiadiazole Derivatives

2020

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“…For recent background literature on the chemistry of related carbazole-derived compounds and their applications, including syntheses of bioactive carbazoles, see: (Chakraborty et al, 1965;Bondock et al, 2019) and references cited therein. The syntheses of related benzo[def]carbazoles are described by Pocock et al (2021) and Geng et al (2016).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and fluorescence of 1-[8-phenyl-9-(phenylethynyl)-4H-benzo[def]carbazol-4-yl]ethan-1-one

Hsiao¹,

Chen²,

Chuang³

2022

Acta Cryst E

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“…The reaction of cyanoacetamide derivative 3 with salicylaldehyde 13aa in ethanol containing piperidine as a catalyst at reflux furnished the coumarin product 281a,b (Scheme 123). 79,134…”

Section: Scheme 122mentioning

confidence: 99%

Synthesis and synthetic applications of cyanoacetamides

Abdelhamid¹,

Ghozlan²,

Abdelmoniem³

et al. 2020

Arkivoc

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Approaches for the preparation of cyanoacetamide derivatives as well as the chemical reactivity profiles and structures of these substances are reviewed. The utility of these compounds as precursors is emphasized in the synthesis of five-and six-membered heterocycles and their fused heterocycles. The reported heterocyclic compounds in this review article are classified according to the kind of the heterocyclic systems.

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Convenient synthesis and antitumor evaluation of some new 9-ethyl-3-(hetaryl)carbazoles

Cited by 12 publications

References 40 publications

Synthesis and In Vitro Antitumor Evaluation of Some Carbazole‐Based Thiazole, Thiophene, and 1,3,4‐Thiadiazole Derivatives

Synthesis and In Vitro Antitumor Evaluation of Some Carbazole‐Based Thiazole, Thiophene, and 1,3,4‐Thiadiazole Derivatives

Crystal structure and fluorescence of 1-[8-phenyl-9-(phenylethynyl)-4H-benzo[def]carbazol-4-yl]ethan-1-one

Synthesis and synthetic applications of cyanoacetamides

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