A New Approach to 3-Indolecarboxaldehyde

Tyson, Floyd T.; Shaw, John T.

doi:10.1021/ja01129a031

Cited by 30 publications

(11 citation statements)

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“…In many reports dimethylformamide were used as a formylating agent for indole [ 25 ], thiophene [ 26 ], and substituted benzene [ 27 ]. Based on these information, we suggested that the reaction was started via formylation of thiazole derivative 6 by DMF to afford the formyl derivative 7 , which involved a reversible opening of the thiazole ring to give intermediate 8 .…”

Section: Resultsmentioning

confidence: 99%

Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents

Mabkhot

Alharbi

Al–Showiman

et al. 2018

Chemistry Central Journal

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BackgroundThe synthesis of new thiazole derivatives is very important because of their diverse biological activities. Also , many drugs containing thiazole ring in their skeletons are available in the market such as Abafungin, Acotiamide, Alagebrium, Amiphenazole, Brecanavir, Carumonam, Cefepime, and Cefmatilen.ResultsEthyl cyanoacetate reacted with phenylisothiocyanate, chloroacetone, in two different basic mediums to afford the thiazole derivative 6, which reacted with dimethylformamide- dimethyl acetal in the presence of DMF to afford the unexpected thiazole derivative 11. The structures of the thiazoles 6 and 11 were optimized using B3LYP/6-31G(d,p) method. The experimentally and theoretically geometric parameters agreed very well. Also, the natural charges at the different atomic sites were predicted. HOMO and LUMO demands were discussed. The anticancer activity of the prepared compounds was evaluated and showed moderate activity.ConclusionsSynthesis of novel thiazole derivatives was done. The structure was established using X-ray and spectral analysis. Optimized molecular structures at the B3LYP/6-31G(d,p) level were investigated. Thiazole derivative 11 has more electropositive S-atom than thiazole 6. The HOMO–LUMO energy gap is lower in the former compared to the latter. The synthesized compounds showed moderate anticancer activity. Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0420-7) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents

Mabkhot

Alharbi

Al–Showiman

et al. 2018

Chemistry Central Journal

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“…Previously, 1H-indole-3-carboxaldehyde (1) has been prepared synthetically either via direct formylation of indole using e.g., Reimer-Tiemann reaction (aq. KOH/CHC l3 ) [17], Grignard reaction [18], Vilsmeier Haack reaction (POCl 3 /DMF) [19] or formylation of the potassium salt of indole using carbon monoxide under robust conditions of heat and pressure [20]. Sommelet reaction on gramine and on indole itself [21] oxidation of N-skatyl-N-phenyl-hydroxylamine [22] and/or by hydrolysis of 3-(1,3-dithiolan-2-yl)indole with boron trifluoride diethyl etherate BF 3 .O(C 2 H 5 ) 2 and mercury (II) oxide HgO [23].…”

Section: Synthetic Methods Of the Preparation Of 1h-indole-3-carboxaldhydementioning

confidence: 99%

1H-Indole-3-carboxaldehyde: Synthesis and Reactions

2017

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“…The [(dimethylamino)methyl]-and [(methylamino)methyl]indoles 5a and 5b were prepared by reductive amination of 5-chloro-1-(4-fluorophenyl)-1H-indol-3-carbaldehyde (4) using dimethylamine and methylamine, respectively, in the presence of sodium cyanoborohydride under standard conditions. 15 The 3-indolecarbal-dehyde 4 was prepared by Vilsmeier formylation [16][17][18] of the corresponding 3-unsubstituted indole. 1 Alkylation of [(methylamino)methyl]indole 5b with 1-(2-chloroethyl)-and 1-(4-chlorobutyl)-2-imidazolidinone afforded 5c and 5d, respectively.…”

Section: Chemistrymentioning

confidence: 99%

“…5-Chloro-and 6-chloro-substituted 2-[1-(4-fluorophenyl)-1H-indol-3-yloxy]acetic acids (17) were prepared in a two-step procedure from corresponding methyl 1-(4fluorophenyl)-3-hydroxy-1H-indole-2-carboxylates (16), which were prepared as described in the literature. 26,27 Alkylation of substituted methyl 1-(4-fluorophenyl)-3-hydroxy-1H-indole-2-carboxylates (16) with methyl bromoacetate gave the corresponding methyl 2-[1-(4-fluorophenyl)-2-(methoxycarbonyl)-1H-indol-3-yloxy]acetates. 26 These diesters were hydrolyzed and subsequently decarboxylated to give the corresponding 2-[1-(4-fluorophenyl)-1H-indol-3-yloxy]acetic acids (17).…”

Section: Chemistrymentioning

confidence: 99%

Serotonin 5-HT₂ Receptor, Dopamine D₂ Receptor, and α₁ Adrenoceptor Antagonists. Conformationally Flexible Analogues of the Atypical Antipsychotic Sertindole

et al. 1996

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Conformationally flexible analogues of the atypical antipsychotic sertindole (1-[2-[4-[5-chloro -1-(4-fluorophenyl)-1H-indol-3-yl]-4-piperidinyl]ethyl]-2-imidazolidi non e) were synthesized. Replacement of the 4-piperidinyl ring in sertindole by a 2-(methylamino)ethoxy group or a 2-(methylamino)ethyl group (e.g. 1-[2-[2-[5-chloro-1-(4-fluorophenyl)-1H -indol-3-yloxy]ethyl-methylamino]ethyl]-2-imidazolidinone and 1-[3-[[2-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl] -ethyl]methylamino]propyl]-2-imidazolidinone results in binding affinities for serotonin 5-HT2A and dopamine D2 receptors, as well as alpha 1 adrenoceptors, which are very similar to those of sertindole. (Methylamino)alkyl groups of other chain lengths, 3-(methylamino)propyloxy groups, and 2-(methylamino)ethylsulfanyl groups do not have such properties. The capability of the 2-(methylamino)ethoxy group and the 2-(methylamino)ethyl group to replace the 4-piperidinyl ring in sertindole is reflected in molecular modeling studies using recently published receptor-interaction models for 5-HT2 and D2 receptors. Structure-affinity investigations concerning the substituents in the indole nucleus and the 2-imidazolidinone ring system in the 2-(methylamino)ethoxy and the 2-(methylamino)ethyl analogues of sertindole have led to high affinity serotonin 5-HT2A receptor antagonists with selectivity versus dopamine D2 receptors and alpha 1 adrenoceptors (e.g. 1-[2-[[2-[6-chloro-1-(4-fluorophenyl) -1H-indol-3-yloxy]ethyl]methylamino]-ethyl]-2-imidazolidinone and 1-[3-[[2-[6-chloro-1-(4-fluorophenyl) -1H-indol-3-yl]ethyl]methylamino]propyl]-2-imidazolidinone). The latter derivative has also high selectivity for 5-HT2A receptors versus serotonin 5-HT2C receptors. Replacement of the basic amino group by nitrogen-containing six-membered rings has led to 5-chloro-1-(4-fluorophenyl)-3-[(4-methylpiperazinyl)-ethoxy]-1H-in dole, which has high affinity for dopamine D2, versus low affinity for serotonin 5-HT2A receptors and alpha 1 adrenoceptors.

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A New Approach to 3-Indolecarboxaldehyde

Cited by 30 publications

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Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents

Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents

1H-Indole-3-carboxaldehyde: Synthesis and Reactions

Serotonin 5-HT₂ Receptor, Dopamine D₂ Receptor, and α₁ Adrenoceptor Antagonists. Conformationally Flexible Analogues of the Atypical Antipsychotic Sertindole

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A New Approach to 3-Indolecarboxaldehyde

Cited by 30 publications

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Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents

Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents

1H-Indole-3-carboxaldehyde: Synthesis and Reactions

Serotonin 5-HT2 Receptor, Dopamine D2 Receptor, and α1 Adrenoceptor Antagonists. Conformationally Flexible Analogues of the Atypical Antipsychotic Sertindole

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Serotonin 5-HT₂ Receptor, Dopamine D₂ Receptor, and α₁ Adrenoceptor Antagonists. Conformationally Flexible Analogues of the Atypical Antipsychotic Sertindole