November 2022 - Page 46 of 81 - Indole Building Blocks

Dalziel, Michael E.’s team published research in Angewandte Chemie, International Edition in 2019 | CAS: 5654-92-2

Angewandte Chemie, International Edition published new progress about Carbamoyl group. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Product Details of C10H13N3.

Dalziel, Michael E. published the artcileRegioselective Functionalization of 7-Azaindole by Controlled Annular Isomerism: The Directed Metalation-Group Dance, Product Details of C10H13N3, the main research area is regioselective functionalization azaindole annular isomerism directed metalation group migration; deuterium; heterocycles; lithiation; regioselectivity; synthetic methods.

The regioselective functionalization of 7-azaindole by controlled annular isomerism employing a directed metalation-group migration is reported. The N7 carbamoyl azaindoles undergo regioselective metalation and quenching with an electrophile to furnish C6-substituted derivatives which, in the presence of a catalytic amount of ClCONR2 promotes a carbamoyl group shift or dance from N7 to N1. A second directed metalation/electrophile quench sequence leads to 2,6-substituted azaindoles. Optimization of the metalation conditions for C2 and C6, sep. and iteratively, is presented. Using the directed metalation group dance strategy, a late-stage deuteration of an antipsychotic drug is described. Overall, the controlled migration of the carbamoyl directing group allows multiple functionalization events of the bioactive azaindole scaffold.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Roever, S.’s team published research in Bioorganic & Medicinal Chemistry Letters in 2005-08-01 | CAS: 104291-81-8

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT2C agonists. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate.

Roever, S. published the artcileIdentification of 4-methyl-1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles as 5-HT2C receptor agonists, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is pyrazinoindole hexahydro preparation 5HT2C receptor agonist.

Synthesis and evaluation of the activity of new 4-methyl-1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles as 5-HT2C receptor agonists are described. Appropriately substituted, several analogs, e.g. I, displayed selectivity against the other 5-HT2 receptor subtypes of 1 order of magnitude or more. Selectivity was improved for several compounds vs. the lead II, increasing the therapeutic interest in this series of 5-HT2C receptor agonists.

Zhou, Mingwei’s team published research in RSC Advances in 2017 | CAS: 71293-59-9

RSC Advances published new progress about Cyclopropanation. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Application of 5,6-Dichloroindolin-2-one.

Zhou, Mingwei published the artcileZinc triflate-mediated cyclopropanation of oxindoles with vinyl diphenyl sulfonium triflate: a mild reaction with broad functional group compatibility, Application of 5,6-Dichloroindolin-2-one, the main research area is spirocyclopropyloxindole preparation; oxindole vinyl diphenyl sulfonium triflate zinc triflate mediated cyclopropanation.

The first use of zinc triflate for the cyclopropanation of unprotected oxindoles with vinyl di-Ph sulfonium triflate salt to afford spiro[cyclopropane-1,3′-indoline]-2′-ones I [R = 5-OH, 6-F, 7-Cl, 4-Br, etc.] was reported. The reaction proceeded under ambient conditions and consistently provided high yields with broad functional group tolerability. The utility for the late-stage functionalization (LSF) of complex mols. was demonstrated.

Qin, Hui’s team published research in Tetrahedron in 2018-11-22 | CAS: 71293-59-9

Tetrahedron published new progress about Cyclopropanation. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Quality Control of 71293-59-9.

Qin, Hui published the artcileA convenient cyclopropanation process of oxindoles via bromoethylsulfonium salt, Quality Control of 71293-59-9, the main research area is oxindole bromoethylsulfonium triflate cyclopropanation; spirocyclopropane indolinone preparation.

A practical convenient conversion of oxindoles into the corresponding spirocyclopropane-oxindoles, e.g., I, is achieved efficiently using bromoethylsulfonium salt, which is easily prepared on a large scale and is stable crystalline This reaction of bromoethylsulfonium salt with different substituted unprotected oxindoles proceeded under mild condition and provided moderate yields.

Haase, F.’s team published research in Tetrahedron Computer Methodology in 1990 | CAS: 41910-64-9

Tetrahedron Computer Methodology published new progress about Computer program. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Formula: C8H8ClN.

Haase, F. published the artcileHeterocyclic reaction design with RDSS, Formula: C8H8ClN, the main research area is computer generated synthetic design heterocyclic compound; RDSS computer program design synthesis heterocycle.

The paper gives a brief description of the synthesis planning computer program RDSS and deals with experience made in application to heterocyclic reactions, e.g., the synthesis of 4-hydroxyindole. The program version RDSS V4.1 was tested after completing a new synthon recognition program. A knowledge base consisting of some general synthesis rules and specialized heterocyclic mechanisms were built up to support this task. The results ensure that the knowledge based system RDSS may be a helpful tool for organic synthesis design.

Beaulieu, Pierre L.’s team published research in Bioorganic & Medicinal Chemistry Letters in 2006-10-01 | CAS: 494799-17-6

Bioorganic & Medicinal Chemistry Letters published new progress about Antiviral agents. 494799-17-6 belongs to class indole-building-block, name is 3-Cyclohexyl-1H-indole-6-carboxylic acid, and the molecular formula is C15H17NO2, Application In Synthesis of 494799-17-6.

Beaulieu, Pierre L. published the artcileImproved replicon cellular activity of non-nucleoside allosteric inhibitors of HCV NS5B polymerase: From benzimidazole to indole scaffolds, Application In Synthesis of 494799-17-6, the main research area is indole derivative preparation antiviral hepatitis C virus polymerase inhibitor.

Benzimidazole-based allosteric inhibitors of the hepatitis C virus (HCV) NS5B polymerase were diversified to a variety of topol. related scaffolds. Replacement of the polar benzimidazole core by lipophilic indoles led to inhibitors with improved potency in the cell-based subgenomic HCV replicon system. Transposing the indole scaffold into a previously described series of benzimidazole-tryptophan amides generated the most potent inhibitors of HCV RNA replication in cell culture reported to date in this series (EC50 ∼ 50 nM).

Chen, Jiong J.’s team published research in Journal of Medicinal Chemistry in 2000-06-15 | CAS: 71293-59-9

Journal of Medicinal Chemistry published new progress about Antiviral agents. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Related Products of indole-building-block.

Chen, Jiong J. published the artcileSynthesis and Antiviral Evaluation of Trisubstituted Indole N-Nucleosides as Analogues of 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB), Related Products of indole-building-block, the main research area is ribofuranosyl chloroindole analog stereochem preparation antiviral cytomegalovirus inhibition; indole nucleoside preparation cytotoxicity virucide structure activity.

2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB) and 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) are nucleosides that exhibit strong and selective activity against human cytomegalovirus (HCMV). Selected polyhalogenated indole nucleosides have now been synthesized as 3-deaza analogs of the benzimidazole nucleosides using the sodium salt glycosylation method. 2-Benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole was prepared stereoselectively via the coupling of a 2-deoxyribofuranosyl α-chloride derivative with the sodium salt of 2-benzylthio-5,6-dichloroindole. This compound was then elaborated into the targeted 2-benzylthio-1-(β-D-ribofuranosyl)-5,6-dichloroindole in five steps. 2,5,6-Trichloro-(1-β-D-ribofuranosyl)indole was prepared using the same synthetic route with 2,5,6-trichloroindole as the starting material. The authors were subsequently able to prepare 2,5,6-trichloro-1-(β-D-ribofuranosyl)indole in three steps using a modification of the sodium salt glycosylation method. 2-Bromo-5,6-dichloro-1-(β-D-ribofuranosyl)indole was also prepared using the same procedures. Target compounds were tested for activity against HCMV, herpes simplex virus type 1 (HSV-1), and human herpes virus six (HHV-6) and for cytotoxicity. All of the compounds were less active against HCMV than TCRB and weakly active or inactive against HSV-1 and HHV-6.

Certal, Victor’s team published research in Bioorganic & Medicinal Chemistry Letters in 2014-03-15 | CAS: 41910-64-9

Bioorganic & Medicinal Chemistry Letters published new progress about Antitumor agents. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, COA of Formula: C8H8ClN.

Certal, Victor published the artcilePreparation and optimization of new 4-(2-(indolin-1-yl)-2-oxoethyl)-2-morpholinothiazole-5-carboxylic acid and amide derivatives as potent and selective PI3Kβ inhibitors, COA of Formula: C8H8ClN, the main research area is indolinyloxoethylmorpholinothiazole carboxylic acid amide derivative phosphatidylinositol kinase inhibitor antitumor; PI3Kβ; PTEN; Thiazole; pAKT.

In the authors’ continuous efforts to identify and develop novel targeted cancer treatments, a new morpholino-thiazole scaffold active against PI3Kβ was identified. This Letter reports the optimization of this compound class to develop PI3Kβ isoform-selective inhibitors with suitable pharmacol. properties.

Iwaki, Yuzo’s team published research in ACS Medicinal Chemistry Letters in 2020-06-11 | CAS: 5654-92-2

ACS Medicinal Chemistry Letters published new progress about Antitumor agents. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Safety of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

Iwaki, Yuzo published the artcileONO-8430506: A Novel Autotaxin Inhibitor That Enhances the Antitumor Effect of Paclitaxel in a Breast Cancer Model, Safety of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is ONO 8430506 autotaxin inhibitor preparation paclitaxel breast cancer.

Lysophosphatidic acid (LPA) is a bioactive lipid mediator that elicits a number of biol. functions, including smooth muscle contraction, cell motility, proliferation, and morphol. change. LPA is endogenously produced by autotaxin (ATX) from extracellular lysophosphatidylcholine (LPC) in plasma. Herein, we report our medicinal chem. effort to identify a novel and highly potent ATX inhibitor, ONO-8430506 (20), with good oral availability. To enhance the enzymic ATX inhibitory activity, we designed several compounds by structurally comparing our hit compound with the endogenous ligand LPC. Further optimization to improve the pharmacokinetic profile and enhance the ATX inhibitory activity in human plasma resulted in the identification of ONO-8430506 (20), which enhanced the antitumor effect of paclitaxel in a breast cancer model.

Certal, Victor’s team published research in Journal of Medicinal Chemistry in 2014-02-13 | CAS: 41910-64-9

Journal of Medicinal Chemistry published new progress about Antitumor agents. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Recommanded Product: 4-Chloroindoline.

Certal, Victor published the artcileDiscovery and Optimization of Pyrimidone Indoline Amide PI3Kβ Inhibitors for the Treatment of Phosphatase and Tensin Homologue (PTEN)-Deficient Cancers, Recommanded Product: 4-Chloroindoline, the main research area is PI3Kbeta phosphatase tensin homolog PTEN neoplasm structure activity preparation.

Compelling mol. biol. publications have reported the implication of phosphoinositide kinase PI3Kβ in PTEN-deficient cell line growth and proliferation. These findings supported a scientific rationale for the development of PI3Kβ-specific inhibitors for the treatment of PTEN-deficient cancers. This paper describes the discovery of 2-[2-(2,3-dihydro-indol-1-yl)-2-oxo-ethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one and the optimization of this new series of active and selective pyrimidone indoline amide PI3Kβ inhibitors. 2-[2-(2-Methyl-2,3-dihydro-indol-1-yl)-2-oxo-ethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one (I), identified following a carefully designed Me scan, displayed improved physicochem. and in vitro pharmacokinetic properties. Structural biol. efforts enabled the acquisition of the first x-ray cocrystal structure of p110β with the selective inhibitor compound I bound to the ATP site. The nonplanar binding mode described herein is consistent with observed structure-activity relationship for the series. Compound I demonstrated significant in vivo activity in a UACC-62 xenograft model in mice, warranting further preclin. investigation. Following successful development, compound 28 entered phase I/Ib clin. trial in patients with advanced cancer.