Month: January 2023

I₂-Triggered N-O cleavage of ketoxime acetates for the synthesis of 3-(4-pyridyl)indoles was written by Gao, Qinghe;Wang, Yakun;Wang, Qianqian;Zhu, Yanping;Liu, Zhaomin;Zhang, Jixia. And the article was included in Organic & Biomolecular Chemistry in 2018.Computed Properties of C9H6ClNO This article mentions the following:

Synthesis of 3-(4-pyridyl)indole derivatives I (R = H, 5-OCH₂C₆H₅, 6-F, 7-NO₂, etc.; R¹ = H, CH₃; Ar = C₆H₅, 2H-1,3-benzodioxol-5-yl, naphthalen-2-yl, etc.) and II from a facile and complementary [3+2+1] annulation of aryl ketoxime acetates Ar(CH₃)C=NOC(O)CH₃ and 1,2,3,4-tetrahydronaphthalen-1-ylideneamino acetate and 3-formylindoles III is reported. The condensation reaction demonstrated that I₂ was capable of triggering N-O bond cleavage of ketoxime acetates to generate iminyl radicals via a single electron transfer pathway. This direct and operationally simple protocol provides a fundamental platform to synthesize 3-(4-pyridyl)indole derivatives I and II with high functional group compatibility and high regioselectivity. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Computed Properties of C9H6ClNO

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 a Series of Diaminoindoles was written by Martin, James S.;Mackenzie, Claire J.;Gilbert, Ian H.. And the article was included in Journal of Organic Chemistry in 2021.Computed Properties of C8H6N2O2 This article mentions the following:

A selection of 3,4-diaminoindoles were required for a recent drug discovery project. To this end, a 10-step synthesis was developed from 4-nitroindole. This synthesis was subsequently adapted and used to synthesize 3,5-; 3,6-; and 3,7-diaminoindoles from the corresponding 5-, 6-, or 7-nitroindole. These novel intermediates feature orthogonal protecting groups that allow them to be further diversified. This is the first reported synthesis of these types of compounds In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Computed Properties of C8H6N2O2

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

Zwitterion-Induced Organic-Metal Hybrid Catalysis in Aerobic Oxidation was written by Hu, Rong-Bin;Lam, Ying-Pong;Ng, Wing-Hin;Wong, Chun-Yuen;Yeung, Ying-Yeung. And the article was included in ACS Catalysis in 2021.Synthetic Route of C8H6N2O2 This article mentions the following:

Herein, an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P⁺-N^–] zwitterionic compound via multiple hydrogen bond interactions was reported. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcs. such as (E)-cinnamyl alc., 4-methoxybenzyl alc., furfuryl alc., etc.; 1,2,3,4-tetrahydroquinoxaline, and indolines I (R = H, 2-Me, 5-Br, 6-NO₂) under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Bronsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Synthetic Route of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Synthetic Route of C8H6N2O2

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

Indolyl Azaspiroketal Mannich Bases Are Potent Antimycobacterial Agents with Selective Membrane Permeabilizing Effects and in Vivo Activity was written by Nyantakyi, Samuel Agyei;Li, Ming;Gopal, Pooja;Zimmerman, Matthew;Dartois, Veronique;Gengenbacher, Martin;Dick, Thomas;Go, Mei-Lin. And the article was included in Journal of Medicinal Chemistry in 2018.Quality Control of 6-Nitro-1H-indole This article mentions the following:

The inclusion of an azaspiroketal Mannich base in the membrane targeting antitubercular 6-methoxy-1-n-octyl-1H-indole scaffold resulted in analogs with improved selectivity and submicromolar activity against Mycobacterium tuberculosis H37Rv. The potency enhancing properties of the spiro-ring fused motif was affirmed by SAR and validated in a mouse model of tuberculosis. As expected for membrane inserting agents, the indolyl azaspiroketal Mannich bases perturbed phospholipid vesicles, permeabilized bacterial cells and induced the mycobacterial cell envelope stress reporter promoter piniBAC. Surprisingly, their membrane disruptive effects did not appear to be associated with bacterial membrane depolarization. This profile was not uniquely associated with azaspiroketal Mannich bases but was characteristic of indolyl Mannich bases as a class. Whereas resistant mycobacteria could not be isolated for a less potent indolyl Mannich base, the more potent azaspiroketal analog displayed low spontaneous resistance mutation frequency of 10-8/CFU. This may indicate involvement of an addnl. envelope-related target in its mechanism of action. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Quality Control of 6-Nitro-1H-indole).

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

Tumor necrosis factor-alpha production-regulating activity of phthalimide derivatives in genetically modified murine melanoma cells B78H1 was written by Orzeszko, Andrzej;Lasek, Witold;Switaj, Tomasz;Stoksik, Magdalena;Kaminska, Beata. And the article was included in Farmaco in 2003.Recommanded Product: 4,5,6,7-Tetrabromoisoindoline-1,3-dione This article mentions the following:

The effect of imides, monothioimides, trimellitimides, as well as 5′-deoxy-5′-phthaloylamino-derivatives of azidothymidine on tumor necrosis factor-alpha (TNF-α) production by genetically modified murine B78H1 melanoma cells transduced with the gene for human TNF-α (B78/TNF) was investigated. It was found that N-(adamant-1-yl)monothiophthalimide and N-(adamant-2-yl)-monothiophthalimide showed over 200% enhancing of TNF-α production while some of imides were inhibitors. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Recommanded Product: 4,5,6,7-Tetrabromoisoindoline-1,3-dione).

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 4,5,6,7-Tetrabromoisoindoline-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

Targeting tubulin polymerization by novel 7-aryl-pyrroloquinolinones: Synthesis, biological activity and SARs was written by Bortolozzi, Roberta;Mattiuzzo, Elena;Dal Pra, Matteo;Sturlese, Mattia;Moro, Stefano;Hamel, Ernest;Carta, Davide;Viola, Giampietro;Ferlin, Maria Grazia. And the article was included in European Journal of Medicinal Chemistry in 2018.Name: 6-Nitro-1H-indole This article mentions the following:

For wide-ranging SARs, a series of 7-arylpyrroloquinolinones, e.g., I (R¹ = Me, Ph, 1-naphthyl, 1,3-benzodioxol-5-yl, etc.; R² = Et, n-C₁₈H₃₇), was synthesized through a robust procedure. For comparison with the reference 3-ethyl-7-phenyl-3H-pyrrolo[3-2-f]quinolin-9-one, the angular geometry and substituents at the 3 and 7 positions were varied to explore interactions inside the colchicine site of tubulin. Among the new compounds synthesized, potent cytotoxicity (low and sub-nanomolar GI₅₀ values) was observed with compounds I (R¹ = 1-naphthyl, 1,3-benzodioxol-5-yl; R² = Et), both more potent than 3-ethyl-7-phenyl-3H-pyrrolo[3-2-f]quinolin-9-one, in both leukemic and solid tumor cell lines. Neither of the two above compounds I induced significant cell death in normal human lymphocytes, suggesting that these compounds may be selectively active against cancer cells. In particular, I (R¹ = 1,3-benzodioxol-5-yl; R² = Et) (II) was a potent inducer of apoptosis in the A549 and HeLa cell lines. With both compounds, induction of apoptosis was associated with dissipation of the mitochondrial transmembrane potential and production of reactive oxygen species, indicating that cells treated with these compounds followed the intrinsic pathway of apoptosis. Moreover, immunoblot anal. revealed that the compound II even at 50 nM reduced the expression of anti-apoptotic proteins such as Bcl-2 and Mcl-1. Finally, mol. docking studies of the newly synthesized compounds demonstrate that active pyrroloquinolinone derivatives strongly bind in the colchicine site of β-tubulin. 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, 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.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

Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis was written by Li, Jian-Yuan;Miklossy, Gabriella;Modukuri, Ram K.;Bohren, Kurt M.;Yu, Zhifeng;Palaniappan, Murugesan;Faver, John C.;Riehle, Kevin;Matzuk, Martin M.;Simmons, Nicholas. And the article was included in Bioconjugate Chemistry in 2019.Computed Properties of C9H6ClNO This article mentions the following:

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chem. conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chem. library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Computed Properties of C9H6ClNO

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

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