Day: January 4, 2023

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones was written by Liu, Yonggui;Luo, Guoyong;Yang, Xing;Jiang, Shichun;Xue, Wei;Chi, Yonggui Robin;Jin, Zhichao. And the article was included in Angewandte Chemie, International Edition in 2020.Recommanded Product: 112656-95-8 This article mentions the following:

The aromatic nitrogen atoms of heteroarylaldehydes were activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products I [R¹ = H, 8′-Br, 7′-Cl, etc.; R² = H, 4-Br, 5-Cl, etc.; R³ = Me, Bn, Trt], II [R¹ = H, 8-Br, 7-F, etc.; R² = H, 3-Me, 4-Cl, etc.; R³ = Me, Et, Ph, Bn, CHPh₂] and III [R¹ = H, 6;t-Bu, 7’Cl, etc.; R² = H, 4-Cl, 5-Me, etc.] were afforded in good to excellent yields and optical purities. Reaction involved the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibited excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichems. for plant protection. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Recommanded Product: 112656-95-8).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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: 112656-95-8

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

Evaluation of 1,2,3-triazoles as amide bioisosteres in cystic fibrosis transmembrane conductance regulator modulators VX-770 and VX-809 was written by Doiron, Jake E.;Le, Christina A.;Ody, Britton K.;Brace, Jonathon B.;Post, Savannah J.;Thacker, Nathan L.;Hill, Harrison M.;Breton, Gary W.;Mulder, Matthew J.;Chang, Sichen;Bridges, Thomas M.;Tang, Liping;Wang, Wei;Rowe, Steven M.;Aller, Stephen G.;Turlington, Mark. And the article was included in Chemistry – A European Journal in 2019.Safety of 6-Nitro-1H-indole This article mentions the following:

The 1,2,3-triazole has been successfully utilized as an amide bioisostere in multiple therapeutic contexts. Based on this precedent, triazole analogs derived from VX-809 and VX-770, prominent amide-containing modulators of the cystic fibrosis transmembrane conductance regulator (CFTR), were synthesized and evaluated for CFTR modulation. Triazole 11, derived from VX-809, displayed markedly reduced efficacy in F508del-CFTR correction in cellular TECC assays in comparison to VX-809. Surprisingly, triazole analogs derived from potentiator VX-770 displayed no potentiation of F508del, G551D, or WT-CFTR in cellular Ussing chamber assays. However, patch clamp anal. revealed that triazole 60 potentiates WT-CFTR similarly to VX-770. The efficacy of 60 in the cell-free patch clamp experiment suggests that the loss of activity in the cellular assay could be due to the inability of VX-770 triazole derivatives to reach the CFTR binding site. Moreover, in addition to the neg. impact on biol. activity, triazoles in both structural classes displayed decreased metabolic stability in human microsomes relative to the analogous amides. In contrast to the many studies that demonstrate the advantages of using the 1,2,3-triazole, these findings highlight the neg. impacts that can arise from replacement of the amide with the triazole and suggest that caution is warranted when considering use of the 1,2,3-triazole as an amide bioisostere. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Safety of 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 6-Nitro-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

Enantioselective Organocatalytic Sulfenylation of β-Naphthols was written by Wang, Jiao-Jiao;Yang, Hui;Gou, Bo-Bo;Zhou, Ling;Chen, Jie. And the article was included in Journal of Organic Chemistry in 2018.COA of Formula: C14H9NO2S This article mentions the following:

An enantioselective sulfenylation of β-naphthols has been developed for the first time using a newly synthesized cinchona-derived thiourea as the catalyst and N-(arylthio) succinimide (or phthalimide) as an electrophilic sulfur source. Various enantioenriched naphthalenones with an S-containing all-substituted stereocenter were prepared via a dearomatization strategy under mild reaction conditions. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

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

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

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

A highly efficient procedure for 3-sulfenylation of indole-2-carboxylates was written by Schlosser, Kevin M.;Krasutsky, Alexei P.;Hamilton, Harriet W.;Reed, Jessica E.;Sexton, Karen. And the article was included in Organic Letters in 2004.HPLC of Formula: 167631-84-7 This article mentions the following:

A highly efficient one-pot procedure for 3-sulfenylation of 2-carboxyindoles is described. Treatment of thiols with N-chlorosuccinimide at -78 °C in CH₂Cl₂ affords sulfenyl chlorides in situ that readily react with 2-carboxyindoles to give 3-thioindoles in high yields. This new method is milder, produces less waste, and is compatible with a wide range of thiol and indole functionality. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7HPLC of Formula: 167631-84-7).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.HPLC of Formula: 167631-84-7

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 3′,4′-Diaryl-4’H-spiro[indoline-3,5′-[1′,2′,4′]oxadiazol]-2-ones via DMAP-catalyzed Domino Reactions and Their Antibacterial Activity was written by Shi, Guanghao;He, Xinwei;Shang, Yongjia;Xiang, Liwei;Yang, Cheng;Han, Guang;Du, Bing. And the article was included in Chinese Journal of Chemistry in 2016.COA of Formula: C11H11NO2 This article mentions the following:

A convenient and metal-free DMAP-catalyzed domino reaction of isatins, arylamines and hydroximoyl chlorides was developed to achieve 1,3-dipolar cycloaddition of imines into aryl nitrile oxides at ambient temperature In this one-pot transformation, a 1,2,4-oxadiazole skeleton was efficiently formed. This methodol. needed no extra additives and features wide substrate scope, good functional group tolerance and mild reaction conditions. A plausible mechanism for this process was proposed. Moreover, the antibacterial activities of the products were evaluated towards Staphylococcus epidermidis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae using the Broth microdilution method. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0COA of Formula: C11H11NO2).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.COA of Formula: C11H11NO2

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

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications was written by Zhao, Lixing;Hu, Chenyang;Cong, Xuefeng;Deng, Gongda;Liu, Liu Leo;Luo, Meiming;Zeng, Xiaoming. And the article was included in Journal of the American Chemical Society in 2021.Name: 6-Nitro-1H-indole This article mentions the following:

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 x 10⁶). Mechanistic studies, based on theor. calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several com. available pharmaceuticals by means of this strategy highlights its potential application in medicinal chem. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) 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.Name: 6-Nitro-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