Month: November 2022

Discovery of 2-(4-sulfonamidophenyl)-indole 3-carboxamides as potent and selective inhibitors with broad hepatitis C virus genotype activity targeting HCV NS4B was written by Zhang, Nanjing;Turpoff, Anthony;Zhang, Xiaoyan;Huang, Song;Liu, Yalei;Almstead, Neil;Njoroge, F. George;Gu, Zhengxian;Graci, Jason;Jung, Stephen P.;Pichardo, John;Colacino, Joseph;Lahser, Fred;Ingravallo, Paul;Weetall, Marla;Nomeir, Amin;Karp, Gary M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Recommanded Product: 5-Fluoro-6-methyl-1H-indole The following contents are mentioned in the article:

A novel series of 2-(4-sulfonamidophenyl)-indole 3-carboxamides was identified and optimized for activity against the HCV genotype 1b replicon resulting in compounds with potent and selective activity. Further evaluation of this series demonstrated potent activity across HCV genotypes 1a, 2a and 3a. Compound I had reduced activity against HCV genotype 1b replicons containing single mutations in the NS4B coding sequence (F98C and V105M) indicating that NS4B is the target. This novel series of 2-(4-sulfonamidophenyl)-indole 3-carboxamides serves as a promising starting point for a pan-genotype HCV discovery program. This study involved multiple reactions and reactants, such as 5-Fluoro-6-methyl-1H-indole (cas: 1000343-16-7Recommanded Product: 5-Fluoro-6-methyl-1H-indole).

5-Fluoro-6-methyl-1H-indole (cas: 1000343-16-7) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 5-Fluoro-6-methyl-1H-indole

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

Mechanistic study of reversible solid-state melt isomerization of 2-oxindoles to 2-quinolinones and its occurrence in a mass spectrometer was written by Martinez-Gudino, Gelacio;Perez-Rojas, Nadia A.;Trujillo-Serrato, Joel J.;Mora-Perez, Yolanda;Suarez-Castillo, Oscar R.;Morales-Rios, Martha S.. And the article was included in Journal of Molecular Structure in 2019.Application In Synthesis of 2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid The following contents are mentioned in the article:

An eco-friendly equilibrated rearrangement of a series of 2-oxo-3-indolyl acetic acids (1) with 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid derivatives (2) was investigated through a solid state melt reaction (SSMR). Mechanistic insight into the thermal rearrangement is provided by ¹³C-isotopic labeling. The standard mass spectra of 1 and 2 were virtually identical preventing their reliable identification. Reversible interconversion of 1 and 2 was evidenced to occur in the inlet system of a mass spectrometer under electron impact conditions. Relative abundances of fragment ions were found to be a function of temperature This study involved multiple reactions and reactants, such as 2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid (cas: 885272-25-3Application In Synthesis of 2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid).

2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid (cas: 885272-25-3) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Application In Synthesis of 2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid

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

Methyleneketenes and methylenecarbenes. V. Condensation of ketones with isopropylidene malonate catalyzed by titanium tetrachloride and synthesis of a dibenzofuran was written by Baxter, Gary J.;Brown, Roger F. C.. And the article was included in Australian Journal of Chemistry in 1975.Reference of 15540-90-6 The following contents are mentioned in the article:

The TiCl4-pyridine-THF reagent of Lehnert will effect direct condensation of some aromatic ketones RCOR1(R = Ph, o-tolyl, 2,5-dimethyl-3-furyl; R1 = Me, Ph, Co2Me, piperidinocarbonyl; RR1 = 2,2′-biphenylylene) with isopropylidene malonate (Meldrum’s acid) to give I. The synthetic value of this reaction is explored in a synthesis of 7-methoxy-9-methyldibenzofuran-3-ol involving pyrolysis of I (R = 2,5-dimethyl-3-furyl), formylation of II with Cl2CHOMe and SnCl4, conversion of III to the 6-MeO analog. condensation with isopropylidene malonate, and pyrolysis of the product. A 1,9-dimethyldibenzofuran related to strepsilin could not be obtained in the same way. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Reference of 15540-90-6).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Reference of 15540-90-6

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

Separation and characterization of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acids by HPLC and GC-MS. Identification in wine samples was written by Herraiz, Tomas;Ough, C. S.. And the article was included in American Journal of Enology and Viticulture in 1994.Quality Control of 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid The following contents are mentioned in the article:

1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acids, products of the reaction of tryptophan and aldehydes in alc. fermented beverages, were isolated by solid phase extraction, analyzed by HPLC, and identified by gas chromatog. and mass spectrometry after derivatization to form N-trifluoroacetyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid Me esters. 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid (THCA) and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (both diastereoisomers) were pos. identified in wine samples. 1-Ethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (ETCA) and 1-isobutyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (IBTCA) were not identified in the wines studied. This study involved multiple reactions and reactants, such as 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (cas: 146436-31-9Quality Control of 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid).

1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (cas: 146436-31-9) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Quality Control of 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

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

The Art of Filling Protein Pockets Efficiently with Octahedral Metal Complexes was written by Blanck, Sebastian;Maksimoska, Jasna;Baumeister, Julia;Harms, Klaus;Marmorstein, Ronen;Meggers, Eric. And the article was included in Angewandte Chemie, International Edition in 2012.Synthetic Route of C15H10BrNO2 The following contents are mentioned in the article:

The design of a metal-based enzyme inhibitor is described here. Its crystallog. anal. of its binding within enzyme active site emphasizes the broad range of possibilities for fitting octahedral metal complexes in an enzyme active site. The simplicity of the structure of complex 1 displays and IC50 value of 83nm (1μM ATP)which is superior to that of FL172, a complex that is much more tedious to synthesize and is of a higher stereochem. complexity (20 possible isomers). The ruthenium phthalimide complex 1 described here is amongst the most potent ATP-competitive inhibitors known for the protein Kinase PAK1. This demonstrates the advantage of filling large or open pockets with globular octahedral metal complexes. This study involved multiple reactions and reactants, such as 2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1Synthetic Route of C15H10BrNO2).

2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Synthetic Route of C15H10BrNO2

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

Access to Multisubstituted Furan-3-carbothioates via Cascade Annulation of α-Oxo Ketene Dithioacetals with Isoindoline-1,3-dione-Derived Propargyl Alcohols was written by Bai, Li-Gang;Chen, Ming-Tao;Xiao, Dong-Rong;Zhao, Liu-Bin;Luo, Qun-Li. And the article was included in Journal of Organic Chemistry in 2018.Recommanded Product: 2-Benzyl-5-bromoisoindoline-1,3-dione The following contents are mentioned in the article:

A Bronsted acid-promoted, unprecedented formal (3 + 2) annulation strategy for the synthesis of multisubstituted furan-3-carbothioates is reported. This transformation represents the first regioselective annulation of α-oxo ketene dithio-acetals as 1,3-bis-nucleophiles in a cascade manner. The choice of isoindoline-1,3-dione-derived propargyl alcs. is crucial to the uncommon annulation mode between an alkyne-type bis-electrophile and a 1,3-bis-nucleophile under metal-free conditions. The scale-up of the synthesis and several interesting transformations of an as-synthesized product were further investigated. A Nazarov-like cyclization is proposed for the ring-closure process according to the exptl. observations. This study involved multiple reactions and reactants, such as 2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1Recommanded Product: 2-Benzyl-5-bromoisoindoline-1,3-dione).

2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 2-Benzyl-5-bromoisoindoline-1,3-dione

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

Malonodiamidines. III. Synthesis and condensation reactions of 1,2,3,4,6,7-hexahydro-7-imino-1,4-dimethyl-5H-1,4-diazepin-5-one was written by Meyer, Horst. And the article was included in Liebigs Annalen der Chemie in 1981.SDS of cas: 15540-90-6 The following contents are mentioned in the article:

[EtOC(:NH)]₂CH₂ reacted with MeNHCH₂CH₂NH₂ to give 2,2′-methylenebis(imidazoline), whereas with MeNHCH₂CH₂NHMe the diazepines I (X = NH, O) were obtained, depending on the amount of H₂O in the reaction. I (X = O) underwent cyclocondensations with mono- and diketones to give II (RR¹ = N:CMeCH:CMe, NHCR²:CR³CHR⁴; R² = Ph, C₆H₄NO₂-3; R³ = CO₂Et, H; R⁴ = Me, Ph) and III (R⁵ = H, 8-Me, 8-Br, R⁶ = H; R⁵ = 8-Me, 9-Cl, 7-Cl, R⁶ = Me). This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6SDS of cas: 15540-90-6).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). SDS of cas: 15540-90-6

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

Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles was written by Liu, Kai;Xu, Guangyang;Sun, Jiangtao. And the article was included in Chemical Science in 2018.Application In Synthesis of tert-Butyl 7-methoxy-1H-indole-1-carboxylate The following contents are mentioned in the article:

An unprecedented dearomatization of indoles with diazoesters was developed via cationic gold(I) catalysis. The functionalization selectively occurred at the C3-position to deliver methylene indole derivatives in good yields with excellent Z-selectivity, demonstrating unusual reactivity and selectivity compared with other noble metal catalysis. Importantly, simply followed by silica gel adsorption, an unprecedented metal-free aerobic oxidation occurred for indoles bearing N-electron donating substituents, provided a novel and efficient approach towards 3-substituted indolin-2-ones with a newly formed quaternary stereocenter in excellent stereoselectivity. Notably, these processes afforded direct and selective access to a variety of valuable intermediates from abundant feedstock chems. This study involved multiple reactions and reactants, such as tert-Butyl 7-methoxy-1H-indole-1-carboxylate (cas: 1215205-77-8Application In Synthesis of tert-Butyl 7-methoxy-1H-indole-1-carboxylate).

tert-Butyl 7-methoxy-1H-indole-1-carboxylate (cas: 1215205-77-8) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of tert-Butyl 7-methoxy-1H-indole-1-carboxylate

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

Cyanomethylation of the Benzene Rings and Pyridine Rings via Direct Oxidative Cross-Dehydrogenative Coupling with Acetonitrile was written by Yao, Hua;Zhong, Xiaoyang;Wang, Bingqing;Lin, Sen;Yan, Zhaohua. And the article was included in Organic Letters in 2022.Product Details of 1190314-60-3 The following contents are mentioned in the article:

A novel and efficient approach for the amine-directed dehydrogenative C(sp₂)-C(sp₃) coupling of arylamines RNH₂ (R = Ph, 5-chloropyridin-2-yl, pyrazin-2-yl, etc.) with acetonitrile was reported by using FeCl₂ as the catalyst. Arylamines react with inactive acetonitrile to form the corresponding arylacetonitriles R¹CH₂CN (R¹ = 2-amino-5-chloropyridin-3-yl, 2-aminophenyl, 6-amino-1,3-benzothiazol-7-yl, etc.) in moderate to good yields. This protocol features nontoxic iron catalysis, efficient atom economy, nonprefunctionalized starting materials, good regioselectivity, and excellent compatibility of functional groups and aromatic rings, providing a novel, straightforward, and green approach toward arylacetonitriles. This study involved multiple reactions and reactants, such as 5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3Product Details of 1190314-60-3).

5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 1190314-60-3

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

Ninhydrin as a building block in scaffold-linked chromophoric dyad construction was written by Margetic, Davor;Mann, David A.;Warrener, Ronald N.. And the article was included in ARKIVOC (Gainesville, FL, United States) in 2014.Reference of 15540-90-6 The following contents are mentioned in the article:

The reaction of ninhydrin with ester-activated cyclobutene epoxide (CE) containing the fused 1,4-dimethoxynaphthalene (DMN) chromophore, gave adducts formed by 1,3-dipolar cycloaddition at the central (C₂)-CO (major) and the outer (C_1,3)-CO (minor) positions. Conversion of the minor adduct to quinoxalines (QIN) by reaction with o-phenylenediamines at the α-dione moiety, albeit in poor yield, led to spiro-DMN-1,4σ-QIN dyad in which the plane of the chromophore was orthogonally oriented yet angled to the plane of the DMN chromophore. Reaction of ninhydrin with o-phenylenediamines yielded the corresponding 11-oxoindeno[1,2-b]quinoxalines which were coupled with CE-BLOCKs to form spiro adducts by reaction at the carbonyl site, the product from CE-1 was identical with that formed above. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Reference of 15540-90-6).

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 15540-90-6

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