Tag: 100-200

A simple and efficient procedure for the one-pot three-component synthesis of spiro[indoline-3,9′-tetrazolo[5,1-b]quinazoline]-2,8′(5’H)-dione in PEG-H₂O medium was written by Shen, Minggui;Wang, Juan;Shang, Shibin;Song, Zhanqian. And the article was included in Chemistry Letters in 2014.Quality Control of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

Novel spiro[indoline-3,9′-tetrazolo[5,1-b]quinazoline]-2,8′(5’H)-dione derivatives I (R¹ = 5-F, 5-OCH₃, 7-F, etc; R² = H, CH₃, C₆H₅) were synthesized by the three-component reaction of isatins II (R² = H, CH₃, C₆H₅) 5-amino-1H-tetrazole and 5,5-dimethylcyclohexane-1,3-dione in PEG-H₂O medium catalyzed by p-TSA. This protocol provides a simple one-step procedure with the advantages of easy work-up, mild reaction conditions and environmental benignity were discussed. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Quality Control of 5,6-Difluoroindoline-2,3-dione).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Quality Control of 5,6-Difluoroindoline-2,3-dione

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

Antioxidant and DNA binding study of 2,2¹-(5,5′-methylenebis(1,3,4-oxadiazole-5,2-diyl)bis(sulfanyl)acetic acid bis(2-oxo-3-indolyl)hydrazides was written by Rani, S. Shobha;Agaiah, Bairi;Sarangapani, M.. And the article was included in International Journal of Chemical Sciences in 2010.COA of Formula: C8H4N2O4 This article mentions the following:

The synthesis of the target compounds was achieved by a reaction of 1H-indole-2,3-dione derivatives with hydrazine and chloroacetyl chloride, formation of 2-chloroacetic acid 2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)hydrazide derivatives, subsequent reaction with 5,5′-methylenebis[1,3,4-oxadiazole-2(3H)-thione] and the products thus obtained were confirmed by elemental anal., IR, NMR, MS. The title compounds were evaluated for their radical scavenging properties using a DPPH radical model [2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazinyl radical] and it was discovered that these compounds displayed antioxidant activity in comparison with ascorbic acid. The compounds were also evaluated in a herring sperm DNA model and it was discovered that these products displayed DNA binding properties in using cisplatin as a drug standard In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8COA of Formula: C8H4N2O4).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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). COA of Formula: C8H4N2O4

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

Synthesis of 4- and 6-substituted nitroindoles was written by Moskalev, Nikolai;Barbasiewicz, Michal;Makosza, Mieczyslaw. And the article was included in Tetrahedron in 2004.Safety of 2-Methyl-6-nitro-1H-indole This article mentions the following:

Enolizable ketones react with m-nitroaniline in the presence of strong base such as tert-BuOK to give 4- and 6-substituted nitroindoles. The reaction proceeds via oxidative nucleophilic substitution of hydrogen in m-nitroaniline with enolate anions in positions ortho to the amino group giving anionic 锜?sup>H adducts that are addnl. stabilized by intramol. interaction between the amino and the carbonyl group. Spontaneous oxidation of the 锜?sup>H adducts followed by the Bayer type condensation of the produced ortho-aminonitrobenzyl ketones gives 4- and 6-substituted nitroindoles. The scope of this reaction and its basic mechanistic features are discussed. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9Safety of 2-Methyl-6-nitro-1H-indole).

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Safety of 2-Methyl-6-nitro-1H-indole

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

[Fe(F₂₀TPP)Cl]-Catalyzed Amination with Arylamines and {[Fe(F₂₀TPP)(NAr)](PhI=NAr)}⁺. Intermediate Assessed by High-Resolution ESI-MS and DFT Calculations was written by Liu, Yungen;Chen, Guo-Qiang;Tse, Chun-Wai;Guan, Xianguo;Xu, Zheng-Jiang;Huang, Jie-Sheng;Che, Chi-Ming. And the article was included in Chemistry – An Asian Journal in 2015.Recommanded Product: 167631-84-7 This article mentions the following:

Amination of C-H bonds catalyzed by transition metal complexes via nitrene/imide insertion is an appealing strategy for C-N bond formation, and the use of iminoiodinanes, or their in situ generated forms from PhI(OAc)₂+primary amides (such as sulfonamides, sulfamates, and carbamates), as nitrogen sources for the amination reaction was well documented. A metal catalyst+PhI(OAc)₂+primary arylamines amination protocol was developed using [Fe(F₂₀TPP)Cl] (H₂F₂₀TPP=meso-tetrakis(pentafluorophenyl)porphyrin) as a catalyst. This catalytic method is applicable for both intra- and intermol. amination of sp² and sp³ C-H bonds (>27 examples), affording the amination products, including natural products such as rutaecarpine, in moderate-to-good yields. ESI-MS anal. and DFT calculations lend support for the involvement of {[Fe(F₂₀TPP)(NC₆H₄-p-NO₂)](PhI=NC₆H₄-p-NO₂)}^+. intermediate in the catalysis. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Recommanded Product: 167631-84-7).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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.Recommanded Product: 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

Design, synthesis, and biological evaluation of N-(3-cyano-1H-indol-5/6-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxamides and 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles as novel xanthine oxidase inhibitors was written by Zhang, Bing;Duan, Yulin;Yang, Yuwei;Mao, Qing;Lin, Fengwei;Gao, Jun;Dai, Xiwen;Zhang, Peng;Li, Qiuhua;Li, Jinxin;Dai, Ronghua;Wang, Shaojie. And the article was included in European Journal of Medicinal Chemistry in 2022.Formula: C8H6N2O2 This article mentions the following:

Xanthine oxidase (XO) has been an important target for the treatment of hyperuricemia and gout. The anal. of potential interactions of pyrimidinone and 3-cyano indole pharmacophores present in the corresponding reported XO inhibitors with parts of the XO active pocket indicated that they both can be used as effective fragments for the fragment-based design of nonpurine XO inhibitors. In this paper, we adopted the fragment-based drug design strategy to link the two fragments with an amide bond to design the type 1 compounds 13a-13w,14c, 14d, 14f, 14g, 14j, 14k, and 15g. Compound 13g displayed an evident XO inhibitory potency (IC₅₀ = 0.16 μM), which was 52.3-fold higher than that of allopurinol (IC₅₀ = 8.37 μM). For comparison, type 2 compounds 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles (25c-25g) were also designed by linking the two fragments with a single bond directly. The results showed that compound 25c from the latter series displayed the best inhibitory potency (IC₅₀ = 0.085 μM), and it was 98.5-fold stronger than that of allopurinol (IC₅₀ = 8.37 μM). These results suggested that amide and single bonds were applicable for linking the two fragments together to obtain potent nonpurine XO inhibitors. The structure-activity relationship results revealed that hydrophobic groups at N-atom of the indole moiety were indispensable for the improvement of the inhibitory potency in vitro against XO. In addition, enzyme kinetics studies suggested that compounds 13g and 25c, as the most promising XO inhibitors for the two types of target compounds, acted as mixed-type inhibitors for XO. Moreover, mol. modeling studies suggested that the pyrimidinone and indole moieties of the target compounds could interact well with key amino acid residues in the active pocket of XO. Furthermore, in vivo hypouricemic effect demonstrated that compounds 13g and 25c could effectively reduce serum uric acid levels at an oral dose of 10 mg/kg. Therefore, compounds 13g and 25c could be potential and efficacious agents for the treatment of hyperuricemia and gout. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: 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

Synthesis and screening of 2-hydroxy-N-(2,41-dioxospiro [indoline-3,21-thiazolidin]-31-yl) benzamides for antiinflammatory activity was written by Devi, N. Saritha;Sarangapani, Manda. And the article was included in International Journal of Pharmacy and Biological Sciences in 2018.SDS of cas: 112656-95-8 This article mentions the following:

A novel synthesis of 2-hydroxy-N-(2,4′-dioxospiro[indoline-3,2′-thiazolidin]-3′-yl)benzamide derivatives I [R = H, 5-F, 5,6-dichloro, etc.] was synthesized by cyclization of isatin hydrazones with thioglycollic acid. The synthesized compounds I were characterized by spectral data (IR, ¹H-NMR, MASS) and evaluated for in-vitro, in-vivo anti-inflammatory activity. The test compounds I exhibited significant potency to inhibit COX-2 enzyme values between 46.23 ± 0.38 to 73.24 ± 0.35, Among the tested compounds compounds I [R = 5,6-dichloro, 5-F, 5-Cl] were considered to possess more potent anti-inflammatory activity when compared to standard drug indomethacin. By in-vitro anti-inflammatory activity the compounds I [R = 5,6-dichloro, 5-F, 5-Cl, 5-Br] were considered to possess more potent anti-inflammatory activity when compared to standard drug indomethacin. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8SDS of cas: 112656-95-8).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 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

Improved synthesis of 3-spiro indolines in dry media under microwave irradiation was written by Dandia, Anshu;Sachdeva, Harshita;Singh, Ruby. And the article was included in Synthetic Communications in 2001.Synthetic Route of C8H4N2O4 This article mentions the following:

The spiro[indole-dipyrrolopyridines] I (X = NH; R = H, Me; R¹, R² = F, H; H, NO₂; Me, Me; NO₂, H; H, NO₂) were prepared in an efficient, one-pot synthesis using microwave irradiation by reaction of spiro[indole-dipyrrolopyrans] I (X = O) with ammonium acetate in the presence of acetic acid. I (X = O) were prepared in situ by microwave induced reaction of indole-2,3-diones and 2-pyrrolidones in a 1:2 molar ratio. Comparative studies were made between microwave irradiation of reactants in the absence of any solvent and catalyzed reactions in the presence of o-dichlorobenzene and classical heating. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Synthetic Route of C8H4N2O4).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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). Synthetic Route of C8H4N2O4

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 and application of P,olefin type axially chiral ligands with sec-alkyl groups was written by Mino, Takashi;Yamaguchi, Daiki;Masuda, Chihiro;Youda, Junpei;Ebisawa, Toshibumi;Yoshida, Yasushi;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2019.Quality Control of 6-Nitro-1H-indole This article mentions the following:

We synthesized N-trans-cinnamyl-N-cyclohexylaniline type aminophosphine 2 and a series of N-2-adamantyl-N-trans-cinnamylaniline type aminophosphines 3. Although aminophosphine 2 failed to find the existence of axial chirality, aminophosphines 3, which exist in the axial chirality in a C(aryl)-N(amine) bond by chiral HPLC anal. as 1-adamantyl type chiral ligands 1. Enantiomeric isomers of 3b, 3c, and 3d were obtained in an enantiomerically pure form. We also identified the palladium-catalyzed asym. allylic substitution of 1,3-diphenyl-2-propenyl acetate with indoles using aminophosphines 3b–d as effective chiral ligands in high enantioselectivities (up to 96% ee). 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 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.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

Carbonylation of doubly lithiated N’-aryl-N,N-dimethylureas: A novel approach to isatins via intramolecular trapping of acyllithiums was written by Smith, Keith;El-Hiti, Gamal A.;Hawes, Anthony C.. And the article was included in Synthesis in 2003.Name: 5-Isopropylindoline-2,3-dione This article mentions the following:

Lithiation of N’-(2-bromoaryl)-N,N-dimethylureas with methyllithium and tert-butyllithium under nitrogen in anhydrous THF at 0 °C gave doubly lithiated arylurea derivatives, which react with carbon monoxide at 0 °C to give isatins in good yields. The scope of the reaction has been demonstrated by application to the synthesis of isatin itself and four substituted isatins bearing alkyl, chloro or fluoro groups. Double lithiation and quenching with ammonium chloride of N‘-(2-bromophenyl)-N,N-dimethylurea gave N‘-(2-bromophenyl)-N,N-dimethylurea. Lithiation of N‘-(2-bromophenyl)-N,N-dimethylurea with methyllithium was followed by addition of (1,1-dimethylethyl)lithium, effecting an bromine-lithium exchange. Sequential carbonylation with carbon monoxide and quenching gave 1H-indole-2,3-dione (isatin). In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Name: 5-Isopropylindoline-2,3-dione).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 5-Isopropylindoline-2,3-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

Co,N-Codoped Porous Carbon-Supported Co_yZnS with Superior Activity for Nitroarene Hydrogenation was written by Zhang, Guangji;Tang, Feiying;Wang, Xiaoying;An, Ping;Wang, Liqiang;Liu, You-Nian. And the article was included in ACS Sustainable Chemistry & Engineering in 2020.Synthetic Route of C8H6N2O2 This article mentions the following:

Preparation of chemoselective hydrogenation catalyst containing both CoNx and CoyZnS supported on N-doped porous carbon (CoN_x-Co_yZnS@NPC-Z) was reported. The CoN_x-Co_yZnS@NPC-Z catalyst were prepared by pyrolyzing the protein-metal-ion networks, followed by treatment with acid. The CoN_x-Co_yZnS@NPC-Z-3 catalyst delivered high catalytic activity and selectivity in chemoselective hydrogenation of nitroarenes afforded aryl amines R-NH₂ [R = Ph, 4-ClC₆H₄, 2-naphthyl, etc.] with almost full conversion and >98% selectivity in water/methanol mixture solvents at 90掳C under 5 bar of H₂ pressure for 3h of reaction. Also Schiff-base derivatives R¹CH=NR² [R¹ = Ph, 4-ClC₆H₄, 4-MeOC₆H₄, etc.; R² = Ph, 2-MeC₆H₄, 4-ClC₆H₄, etc.] were prepared via one-pot reductive amination of aryl aldehydes with aromatic nitro compounds using CoN_x-Co_yZnS@NPC-3 catalyst. Notably, the catalytic hydrogenation could work even under 1 bar of H₂ pressure and at room temperature with high conversion and selectivity. Besides, CoN_x-Co_yZnS@NPC-Z-3 exhibited remarkable tolerance to CO or H₂S poisoning and acid erosion. 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. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. 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). Synthetic Route of C8H6N2O2

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