17954-05-1

Upstream product

• 103-71-9 phenyl isocyanate 
• 82414-26-4 (1H-Indol-2-yl)-phenyl-methanone oxime 
• 26340-49-8 2-iodo-1H-indole 
• 201230-82-2 carbon monoxide 
• 62-53-3 aniline 
• 1477-50-5 Indole-2-carboxylic acid 
• 1022-86-2 2-benzoylindole 
• 13307-67-0 ethyl 1H-indole-1-carboxylate 
• 82414-18-4 3-Phenyl-3a,8b-dihydro-isoxazolo[4,5-b]indole-4-carboxylic acid ethyl ester 
• 3770-50-1 2-carbethoxyindole 
• 58881-45-1 Indole-2-carbonyl chloride 
• 36193-65-4 1H-indole-2-carbonitrile 
• 66003-76-7 Diphenyliodonium triflate 
• 3419-91-8 N-(2-pyridyl)indole 

Downstream Products

• 1084920-03-5 N-(1H-indol-2-ylmethyl)-N-phenylamine 
• 62048-33-3 N-methyl-N-phenyl-1-methyl-1H-indole-2-carboxamide 

Relevant academic research and scientific papers

Chemoselective Cu-catalyzed synthesis of diverseN-arylindole carboxamides, β-oxo amides andN-arylindole-3-carbonitriles using diaryliodonium salts

Chemoselective copper-catalyzed synthesis of diverseN-arylindole-3-carboxamides, β-oxo amides andN-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, α-cyano ketones and diaryliodonium salts has been developed. DiverseN-arylindole-3-carboxamides and β-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition of an organic base (DIPEA) resulted in a completely different selectivity pattern to produceN-arylindole-3-carbonitriles. Moreover, the importance of the developed methodology was realized by the synthesis of indoloquinolones andN-((1H-indol-3-yl)methyl)aniline and by a single-step gram-scale synthesis of the naturally occurring cephalandole A analogue.

Synthesis of Indolo[2,3- c]quinolin-6(7 H)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C-H Arylation

The synthesis of variously substituted indolo[2,3-c]quinolin-6(7H)-ones was developed via Pd-catalyzed intramolecular C-H arylation. This method highlights a strategy for preparing indoloquinoline precursors bearing versatile functional groups and provide

HETEROCYCLIC CARBOXYLIC ACID AMIDE LIGAND AND APPLICATIONS THEREOF IN COPPER CATALYZED COUPLING REACTION OF ARYL HALOGENO SUBSTITUTE

Provided are a heterocyclic carboxylic acid amide ligand and applications thereof in a copper catalyzed coupling reaction. Specifically, provided are uses of a compound represented by formula (I), definitions of radical groups being described in the specifications. The compound represented by formula (I) can be used as the ligand in the copper catalyzed coupling reaction of the aryl halogeno substitute, and is used or catalyzing the coupling reaction for forming the aryl halogeno substitute having C—N, C—O, C—S and other bonds.

1H-indole-2-carboxamide derivative and preparation method and applications thereof

The invention belongs to the technical field of medicine, and discloses a 1H-indole-2-carboxamide derivative of a formula (I) and a preparation method thereof. The preparation method includes the following steps: a compound of a formula (II) and sodium hydroxide are subjected to a hydrolysis reaction to synthetize a compound of a formula (III); the compound of the formula (III) and H2NR2 are subjected to an amidation reaction to synthetize a compound of a formula (IV); the compound of the formula (IV) and halogenated R1 are subjected to a nucleophilic substitution reaction to synthetize a compound of a formula (V); the compound of the formula (V) and a selectfluor are subjected to an electrophilic substitution reaction to synthetize a compound of a compound (VI), and the compound of the formula (VI) and the halogenated R1 are subjected to the nucleophilic substitution reaction to synthetize the compound of the formula (I). The 1H-indole-2-carboxamide derivative of the formula (I) is aagonist with high affinity, selectivity and activity for CB2 receptors, and can be potentially used for treating a plurality of diseases such as multiple sclerosis, autoimmune diseases, osteoporosis,arthralgia, inflammatory pain, and neurodegenerative diseases.

Amidoalkylindoles as Potent and Selective Cannabinoid Type 2 Receptor Agonists with in Vivo Efficacy in a Mouse Model of Multiple Sclerosis

Selective CB2 agonists represent an attractive therapeutic strategy for the treatment of a variety of diseases without psychiatric side effects mediated by the CB1 receptor. We carried out a rational optimization of a black market designer drug SDB-001 that led to the identification of potent and selective CB2 agonists. A 7-methoxy or 7-methylthio substitution at the 3-amidoalkylindoles resulted in potent CB2 antagonists (27 or 28, IC50 = 16-28 nM). Replacement of the amidoalkyls from 3-position to the 2-position of the indole ring dramatically increased the agonist selectivity on the CB2 over CB1 receptor. Particularly, compound 57 displayed a potent agonist activity on the CB2 receptor (EC50 = 114-142 nM) without observable agonist or antagonist activity on the CB1 receptor. Furthermore, 57 significantly alleviated the clinical symptoms and protected the murine central nervous system from immune damage in an experimental autoimmune encephalomyelitis (EAE) mouse model of multiple sclerosis.

Cationic Rhodium(III)-Catalyzed Direct C-2 Carboxamidation of Indoles with Isocyanates via C-H Bond Functionalization

A pentamethylcyclopentadienylrhodium(III)-catalyzed regioselective synthesis of indole-2-carboxamides is described employing N-pyrimidylindoles and isocyanates as coupling partners via C-H functionalization. A wide variety of indole-2-carboxamides can be

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D2 Receptor Through Fragmentation of a Bitopic Ligand

Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652) (1) adopts a bitopic pose at one protomer of a dopamine D2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.

Manganese(I)-Catalyzed C-H Aminocarbonylation of Heteroarenes

A versatile manganese(I) catalyst was employed in C-H aminocarbonylation reactions of heteroarenes with aryl as well as with alkyl isocyanates using a removable directing group approach. Detailed experimental mechanistic studies were suggestive of an organometallic C-H manganesation step, followed by a rate-determining migratory insertion. Heteroaromatic amides were obtained by a step-economical, manganese(I)-catalyzed C-H aminocarbonylation reaction between heteroarenes and aryl and alkyl isocyanates. The catalytic cycle was initiated by a facile organometallic C-H manganesation step, followed by a rate-determining migratory insertion.

Synthesis, structure-activity relationships and molecular modeling studies of new indole inhibitors of monoamine oxidases A and B

New monoamine oxidase inhibitors were synthesized as indole analogues of a previously reported pyrrole series. Several compounds were potent MAO-A (12, 17, 19-22, 31, 36, and 37) or MAO-B (14, 20, 24, 38, 44, and 46) inhibitors, and had Ki values in the nanomolar concentration range. In particular, 22 (Ki = 0.00092 μM, and SI = 68,478) was exceptionally potent and selective as MAO-A inhibitor. In molecular modeling studies, compounds 22, 24, 44, and 46 positioned the indole ring into an aromatic cavity of MAO-A, and established π-π stacking interactions with Tyr407, Tyr444, and FAD cofactor. However, only compound 22 was able to form hydrogen bonds with FAD, a finding which was in accordance with its potent anti-MAO-A activity. Conversely, 22/MAOB complex was highly unstable during the MD simulation.

Bis(1H-2-indolyl)methanones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase

The novel lead bis(1H-2-indolyl)methanone inhibits autophosphorylation of platelet-derived growth factor (PDGF) receptor tyrosine kinase in intact cells. Various substituents in the 5- or 6-position of one indole ring increase or preserve potency, whereas