1211-35-4

Usage

InChI:InChI=1/C14H10ClN/c15-12-7-5-10(6-8-12)14-9-11-3-1-2-4-13(11)16-14/h1-9,16H

Upstream product

• 3282-33-5 1-(4-chlorophenyl)-2-diazoethanone 
• 62-53-3 aniline 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 100-61-8 N-methylaniline 
• 172983-88-9 1-(4-chlorophenyl)-2-(methyl(phenyl)amino)ethanone 
• 19158-57-7 (2-(4-chlorophenyl)-2-oxoethyl)dimethylsulfonium bromide 
• 106-39-8 bromochlorobenzene 
• 75400-67-8 indole-1-carboxylic acid tert-butyl ester 
• 99-91-2 para-chloroacetophenone 
• 100-63-0 phenylhydrazine 
• 57845-08-6 p-chloroacetophenone phenylhydrazone 
• 42472-69-5 4-ethynylacetophenone 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 2447-94-1 N-(p-chlorobenzoyl)-o-toluidine 

Downstream Products

• 102451-68-3 2-(4-chlorophenyl)-3-(2-nitro-1-phenylethyl)-1H-indole 
• 23746-90-9 2-(4-chloro-phenyl)-indol-3-one oxime 
• 88151-96-6 C₂₁H₁₇ClN₆O₂S 
• 88151-94-4 4-[2-(4-Chloro-phenyl)-1H-indol-3-ylazo]-N-pyrimidin-2-yl-benzenesulfonamide 
• 88151-95-5 4-[2-(4-Chloro-phenyl)-1H-indol-3-ylazo]-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide 
• 1217-83-0 2-(4-chlorophenyl)-1H-indole-3-carbaldehyde 
• 5905-11-3 2-(4-chlorophenyl)-1-methyl-2-phenyl-1H-indole 
• 88152-05-0 C₂₁H₁₉ClN₆O₂S 
• 88152-03-8 4-{N'-[2-(4-Chloro-phenyl)-1H-indol-3-yl]-hydrazino}-N-pyrimidin-2-yl-benzenesulfonamide 
• 88152-04-9 4-{N'-[2-(4-Chloro-phenyl)-1H-indol-3-yl]-hydrazino}-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide 
• 924233-18-1 2-chloro-1-(2-(4-chlorophenyl)-1H-indol-3-yl)ethanone 
• 1224200-10-5 3-chloro-5,6-diphenylindolo[2,1-a]isoquinoline 
• 1228020-27-6 C₂₈H₂₀ClN 
• 1262302-55-5 2,2'-bis(4-chlorophenyl)-1H,1'H-3,3'-biindole 

Relevant academic research and scientific papers

Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2- bromotrifluoroacetanilides

(Chemical Equation Presented) Cross-coupling of 1-alkynes with vinyl iodides occurs at 80°C in dioxane catalyzed by CuI/N,N-dimethylglycine to afford conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne, 2 mol % of CuI, 6 mol % of L-proline, and K2CO3 in DMF at 80 °C leads to the formation of the corresponding indole. This conversion involves a CuI/L-proline-catalyzed coupling between aryl bromide and the 1-alkyne followed by a CuI-mediated cyclization process. An ortho-substituent effect directed by NHCOCF3 enables me reaction to proceed under these mild conditions. Both aryl acetylenes and O-protected propargyl alcohol can be applied, leading to 5-, 6-, or 7-substituted 2-aryl and protected 2-hydroxymethyl indoles in good yields. With simple aliphatic alkynes, however, lower yields were observed.

Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents

A novel series of twenty 3-thiocyanato-1H-indoles, carrying diversification at positions N-1, C-2 and C-5 of the heterocyclic core, were synthesized; their antiproliferative activity against four human cancer cell lines (HL60, HEP-2, NCI-H292 and MCF-7) was evaluated, employing doxorubicin as positive control. Indole, N-methylindole and 2-(4-chlorophenyl)-N-methylindole demonstrated to be essentially inactive, whereas several of their congener 3-thiocyanato-1H-indoles displayed good to excellent levels of potency (IC50 ≤ 6 μM), while being non-hemolytic. N-Phenyl-3-thiocyanato-1H-indole and 1-methyl-2-(4-chlorophenyl)-3-thiocyanato-1H-indole showed good to high potency against all the cell lines. On the other side, the N-(4-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-phenyl- 3-thiocyanato-1H-indole derivatives were slightly less active against the test cell lines. Overall, these results suggest that the indole-3-thiocyanate motif can be suitably decorated to afford highly cytotoxic compounds and that the substituted indole can be employed as a useful scaffold toward more potent compounds.

Discovery of indole-based tetraarylimidazoles as potent inhibitors of urease with low antilipoxygenase activity

A series of tetraarylimidazoles (5A-5O) were prepared by one pot four component condensation reactions of 2-arylindole-3-carbaldehydes, substituted anilines, benzil and ammonium acetate in acetic acid. The synthesized compounds exhibited potent antiurease

Gold-catalyzed synthesis of 2-substituted, 2,3-disubstituted and 1,2,3-trisubstituted indoles in [bmim]BF4

Cyclization of 2-alkynylanilines in the presence of NaAuCl 4·H2O using [bmim]BF4 as the reaction medium afforded 2-substituted indoles in high yields. The catalyst system was best recycled using n-Bu4NAuCl4. 2,3-Disubstituted indoles could be prepared from 2-alkynylanilines and 3-buten-2-one through a one-flask annulation-alkylation sequence and 1,2,3-trisubstituted indoles were obtained from the same starting materials via an aza-Michael addition-annulation- alkylation process. Georg Thieme Verlag Stuttgart.

Iron-Catalyzed Reductive Cyclization of o-Nitrostyrenes Using Phenylsilane as the Terminal Reductant

Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene.

Catalytic Tandem Friedel-Crafts Alkylation/C4-C3 Ring-Contraction Reaction: An Efficient Route for the Synthesis of Indolyl Cyclopropanecarbaldehydes and Ketones

A general strategy for the synthesis of indolyl cyclopropanecarbaldehydes and ketones via a Br?nsted acid-catalyzed indole nucleophilic addition/ring-contraction reaction sequence has been exploited. The procedure leads to a wide panel of cyclopropyl carbonyl compounds in generally high yields with a broad substrate scope.

Pd-Catalyzed cascade reaction for the synthesis of 2-substituted indoles

An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles.

Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors

New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized 5. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCI/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.

Preparation of some novel imidazopyridine derivatives of indole as anticancer agents: one-pot multicomponent synthesis, biological evaluation and docking studies

A series of novel imidazopyridine derivatives of indole has been synthesized. All the synthesized derivatives were evaluated for their antiproliferative activity against A-549, T-47D, Hep-G2 and MCF-7 human cancer cell lines. The results demonstrated that some of these derivatives exhibited moderate to excellent cytotoxic activities. Compounds 7a having a cyclohexyl ring substituted to the second amine of imidazopyridyl moiety and phenyl ring of the C-2 indole ring and 7f with a para-methylphenyl ring at the same position exhibited the highest activity against the A-594 cell line with IC50 of 11.48?μM and 10.66?μM, respectively. The results indicate that compounds 7a and 7f are more cytotoxic towards cancer cell lines compared with etoposide in vitro. In addition, compounds, 7d and 7j showed the most potent activity against Hep-G2, equal to etoposide as the standard drug. Also, most of the compounds were inactive against the T-47D and MCF-7 cell lines. The morphological analysis by the acridine orange/ethidium bromide double-staining test and flow cytometry analysis indicated that compounds 7a and 7f induced apoptosis in A-549 cells. Furthermore, in silico and in vitro results of the synthesized compounds showed good correlation with each other. Molecular docking results of the compounds of the 7a–k series with the cyclohexyl ring substituted to the second amine of the imidazopyridyl moiety compared with the 7l–t members with the t-butyl group at the same position confirmed the effect of the higher lipophilicity on hydrophobic interactions with the studied enzymes. Moreover, all the compounds showed higher affinity to tubulin than topoisomerase IIα enzyme.

Synthesis of indoles: Sulfur-assisted reaction of 2-nitrostilbenes with carbon monoxide

When 2-nitrostilbenes were treated with carbon monoxide in the presence of elemental sulfur, the reductive N-heterocyclization of the 2-nitrostilbenes smoothly proceeded to give the corresponding indoles in moderate to good yields.