Tag: 200-300

Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds was written by Huang, Xi;Li, Juan;Li, Xiang;Wang, Jiayi;Peng, Yanqing;Song, Gonghua. And the article was included in RSC Advances in 2019.Application of 14204-27-4 This article mentions the following:

A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective α-sulfenylation/β-thiolation of α,β-unsaturated carbonyl compds R¹CH=CHC(O)R² (R¹ = C₆H₅, furan-2-yl, 2H-1,3-benzodioxol-5-yl, etc.; R² = CH₃, C₆H₅, 4-FC₆H₄, etc.). An aromatic sulfur group could be chemoselectively introduced at α- or β-position of carbonyls with different sulfur reagents R³SSR³ (R³ = C₆H₅, 4-CH₃C₆H₄, 4-CH₃OC₆H₄, 4-FC₆H₄) under slightly changed reaction conditions. A series of desired products (Z) and (E)-R¹CH=C(SPh)C(O)R² and R¹CH(SR³)CH₂C(O)R² were obtained in moderate to excellent yields. Mechanistic studies revealed that B₂pin₂ played the key role in activating the transformation towards the β-thiolation of α,β-unsaturated carbonyl compounds This transition-metal-catalyst-free method provides a convenient and efficient tool for the highly chemoselective preparation of α-thiolation or β-sulfenylation products of α,β-unsaturated carbonyl compounds In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application of 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Application of 14204-27-4

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

Discovery of 3,4-Dihydrobenzo[f][1,4]oxazepin-5(2H)-one Derivatives as a New Class of Selective TNIK Inhibitors and Evaluation of Their Anti-Colorectal Cancer Effects was written by Li, Yueshan;Zhang, Liting;Yang, Ruicheng;Qiao, Zeen;Wu, Ming;Huang, Chong;Tian, Chenyu;Luo, Xinling;Yang, Wei;Zhang, Yun;Li, Linli;Yang, Shengyong. And the article was included in Journal of Medicinal Chemistry in 2022.Computed Properties of C13H17BN2O2 This article mentions the following:

The Traf2- and Nck-interacting protein kinase (TNIK) is a downstream signal protein of the Wnt/β-catenin pathway and has been thought of as a potential target for the treatment of colorectal cancer (CRC) that is often associated with dysregulation of Wnt/β-catenin signaling pathway. Herein, we report the discovery of a series of 3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one derivatives as a new class of TNIK inhibitors. Structure-activity relationship (SAR) analyses led to the identification of a number of potent TNIK inhibitors with compound 21k being the most active one (IC₅₀: 0.026 ± 0.008 μM). This compound also displayed excellent selectivity for TNIK against 406 other kinases. Compound 21k could efficiently suppress CRC cell proliferation and migration in in vitro assays and exhibited considerable antitumor activity in the HCT116 xenograft mouse model. It also showed favorable pharmacokinetic properties. Overall, 21k could be a promising lead compound for drug discovery targeting TNIK and deserves further studies. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Computed Properties of C13H17BN2O2).

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Computed Properties of C13H17BN2O2

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

Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins was written by Denmark, Scott E.;Chi, Hyung Min. And the article was included in Journal of the American Chemical Society in 2014.Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

A method for the enantioselective, intramol. sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide Lewis base catalyst [e.g., I + PhthSPh → II (93% yield, e.r. 93.6:6.4)]. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and high enantiomeric ratios via enantioselective formation and subsequent stereospecific capture of the thiiranium intermediate with the pendant tosyl-protected amine. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application In Synthesis of 2-(Phenylthio)isoindoline-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

Determinations with polyaldehydes. IV. Fluorescence of 2-phenylphthalimidines was written by Amano, Tameyuki;Sakano, Toshiyuki;Mizukami, Satoshi. And the article was included in Yakugaku Zasshi in 1965.Application of 5388-42-1 This article mentions the following:

Following I are synthesized and their fluorescence ability examined Thus, a mixture of 536 mg. ο-phthalaldehyde and 436 mg. ο-aminophenol is kept for 3 weeks in 100 ml. Et₂O, 90 ml. solvent removed, the precipitated mass dissolved in C₆H₆, chromatographed on 12 Al₂O₃, and eluted with C₆H₆ to give 44 mg. I (R = ο-OH), needles, m. 166.5° (C₆H₆-Et₂O). Similarly are prepared the following I (R and m.p. given): m-OH, 202-3° (MeOH); p-OH, 221-3° (MeOH); m-OMe, 130-1° (MeOH); p-OMe, 139° (MeOH); m-Me, 145° (Et₂O); p-Me, 139-40° (C₆H₆); ο-Cl, 172-3° (EtOH); m-Cl, 185.5° (MeOH); p-Cl, 184-5° (dioxane); m-Br, 186-7° (dioxane-MeOH); p-Br, 183° (dioxane); m-I, 171° (dioxane); p-I, 200-1° (dioxane); ο-CO₂H, 248-50° (MeOH); m-CO₂H, 282-3° (dioxane); p-CO₂H, <300° (EtOH-dioxane); ο-NO₂, 164° (dioxane); m-NO₂, 237-8° (dioxane); p-NO₂, 236° (dioxane) (yellow); 2′,3′-benzo, 194-5° (C₆H₆); 3′,4′-benzo, 188-9° (C₆H₆). Fluorescence of I requires the conjugation of phthalimidine ring and Ph group, and there is a great contribution of ionic resonance structure. Extension of the conjugated system increased fluorescence ability while interference of planar configuration by steric hindrance decreased or completely inhibited fluorescence. This fluorescence ability is affected by the electronic character of the substituent in the Ph ring; increased electron-donating nature of the substituent resulted in the red shift of the maximum wave length and decrease in fluorescence intensity, while increased electron-accepting nature of the substituent resulted in the blue shift of the maximum wave length and increase in fluorescence intensity. Introduction of a NO₂ group completely inhibited fluorescence ability of 2-phenylphthalimidine. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application of 5388-42-1

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

Synthesis of 1H-indole-3-carbonitrile derivatives was written by Yang, Yan-mei;Ge, Yu-hua. And the article was included in Huaxue Shiji in 2008.Related Products of 90271-86-6 This article mentions the following:

A method for the synthesis of the title compounds is reported here. A one-step synthesis of 5-substituted 1H-indole-3-carbonitrile derivatives was carried out using 5-substituted 1H-indole-3-carboxaldehyde and hydroxylamine hydrochloride under acidic condition. The products were identified by m.p. determination, IR and ¹HNMR. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Related Products of 90271-86-6).

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Related Products of 90271-86-6

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

Copper-mediated C3-cyanation of indoles by the combination of amine and ammonium was written by Liu, Bin;Wang, Jiehui;Zhang, Bo;Sun, Yang;Wang, Lei;Chen, Jianbin;Cheng, Jiang. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2014.Related Products of 90271-86-6 This article mentions the following:

A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N’,N’-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H₂O followed by hydrolysis to form the aldehyde. Then the reaction between the aldehyde and ammonium afforded nitriles. The reaction employs O₂ as a clean oxidant with good efficiency and functional group tolerance. Thus, it represents a facile and safe procedure leading to 3-cyano indoles. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Related Products of 90271-86-6).

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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). Related Products of 90271-86-6

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

Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen Radicals was written by Morcillo, Sara P.;Dauncey, Elizabeth M.;Kim, Ji Hye;Douglas, James J.;Sheikh, Nadeem S.;Leonori, Daniele. And the article was included in Angewandte Chemie, International Edition in 2018.Electric Literature of C14H9NO2S This article mentions the following:

The selective functionalization of C(sp³)-H bonds at distal positions to functional groups is a challenging task in synthetic chem. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5-H-atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late-stage functionalization of amino acids and a dipeptide. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Electric Literature of C14H9NO2S).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Electric Literature of C14H9NO2S

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

Discovery of a potent, orally available dual CysLT₁ and CysLT₂ antagonist with dicarboxylic acid was written by Itadani, Satoshi;Takahashi, Shinya;Ima, Masaki;Sekiguchi, Tetsuya;Aratani, Yoshiyuki;Egashira, Hiromu;Matsumura, Naoya;Inoue, Atsuto;Yonetomi, Yasuo;Fujita, Manabu;Nakayama, Yoshisuke;Takeuchi, Jun. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Recommanded Product: 89245-41-0 This article mentions the following:

A potent, orally available dual CysLT₁ and CysLT₂ receptor antagonist with a dicarboxylic acid is described. 4-(3-(Carboxymethyl)-4-{(E)-2-[4-(4-phenoxybutoxy)phenyl]vinyl}-1H-indol-1-yl)butanoic acid (15: ONO-4310321, IC₅₀: CysLT₁ = 13 nM, CysLT₂ = 25 nM) showed excellent pharmacokinetic profiles (%F_rat = 100) compared with our previously reported compound 1 (%F_rat = 1.5). In addition, we describe a new rule for dicarboxylic acid derivatives to show good oral bioavailability (%F_rat ≥ 40) in rats (HBDs: ≤2, C log P: >6.5 and TPSA: <100). Especially, reduction of only one hydrogen-bond donor (HBDs) showed dramatically improved oral bioavailability. This small change of HBDs in dicarboxylic acid derivatives is generally a very effective modification. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Recommanded Product: 89245-41-0).

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. 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: 89245-41-0

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 Rh(II)-catalyzed formal N-S bond insertion reaction of aryldiazoacetates into N-phenyl-sulfenyl phthalimide was written by Song, Zhuang;Wu, Yizhou;Xin, Tao;Jin, Chao;Wen, Xiaoan;Sun, Hongbin;Xu, Qing-Long. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2016.Synthetic Route of C14H9NO2S This article mentions the following:

The Rh(II)-catalyzed sulfur ylide [1,2]-rearrangement of carbenoids generated from aryldiazoacetates has been realized via N-S bond insertion, generating tertiary sulfides in moderate to excellent yields. This demonstrates the first use of the sulfur ylide [1,2]-rearrangement undergoing N-S bond insertion. This protocol could proceed smoothly with high regioselectivity, low catalyst loading (0.1 mol% Rh₂(OAc)₄), gram-scale reaction and broad substrate scope. And the product could be converted into glycine derivatives through simple procedures. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Synthetic Route of C14H9NO2S).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Synthetic Route of C14H9NO2S

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

Reaction of arylhalodiazirines with thiophenoxide: a redox process was written by Creary, Xavier;Sky, Anthony F.;Phillips, Gillian;Alonso, David E.. And the article was included in Journal of the American Chemical Society in 1993.Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Phenylbromodiazirine reacts with thiophenoxide ion in methanol to give benzonitrile, benzamidine, ammonia, and di-Ph disulfide. The reaction is general for arylhalodiazirines, with electron-withdrawing groups on the aromatic ring exerting a small rate-enhancing effect. Three potential mechanisms are suggested for this redox process. These mechanisms include an N-sulfenylated diazirine, a diazirinyl radical, and diazirinyl anion. Ring opening of these intermediates and subsequent transformations would lead to benzonitriles, benzamidine, and ammonia. A key intermediate in these transformations is PhSNH₂. This intermediate has been independently generated and found to rapidly convert to ammonia and di-Ph disulfide under the reaction conditions. Another proposed intermediate, N-(phenylthio)benzamidine, has also been independently generated and subjected to the reaction conditions, where benzamidine and more di-Ph disulfide result. Theor. calculations suggest the existence of isomeric diazirinyl anions. In addition to a diazirinyl ion with charge essentially on carbon, there is also an allylic-type ion with charge on the two nitrogen atoms. Single-electron reduction of a diazirinyl radical necessarily leads to a nitrogen-centered diazirinyl anion. Conversion of this anion to the carbon-centered diazirinyl anion is a forbidden process. These theor. studies suggest that the diazirinyl anion may be a viable intermediate in solution In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 2-(Phenylthio)isoindoline-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