January 2023 - Page 17 of 26 - Indole Building Blocks

Lakshmi Reddy, Vanammoole et al. published their research in New Journal of Chemistry in 2018 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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 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). Category: indole-building-block

An efficient synthesis of versatile synthon 3-chlorooxindoles with NaCl/oxone was written by Lakshmi Reddy, Vanammoole;Prathima, Parvathaneni Sai;Rao, Vaidya Jayathirtha;Bikshapathi, Raktani. And the article was included in New Journal of Chemistry in 2018.Category: indole-building-block This article mentions the following:

The present work describes an expedient approach for the direct conversion of indole-3-carboxaldehyde to 3-chlorooxindoles, e.g., I using a simple sustainable synthetic method. From an environmental perspective, a combination of NaCl/oxone in a CH₃CN:H₂O (1:1) system was developed for direct oxidative chlorination of a wide array of indole derivatives This chlorination strategy is more viable, remarkably cheaper and provides easy access to potential 3-chlorooxindoles. In addition, this environmentally benign method can also be applicable for constructing isatin derivatives in good yields. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).

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

Yang, Yan-mei et al. published their research in Huaxue Shiji in 2008 | CAS: 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

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).

Amano, Tameyuki et al. published their research in Yakugaku Zasshi in 1965 | CAS: 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

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).

Gupta, Swati et al. published their research in MedChemComm in 2013 | CAS: 827-01-0

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

Identification of novel urea derivatives as PTP1B inhibitors: synthesis, biological evaluation and structure-activity relationships was written by Gupta, Swati;Varshney, Kanika;Srivastava, Rohit;Rahuja, Neha;Rawat, Arun K.;Srivastava, Arvind K.;Saxena, Anil K.. And the article was included in MedChemComm in 2013.Computed Properties of C9H6ClNO This article mentions the following:

The protein tyrosine phosphatase 1B (PTP1B) is an attractive target for the treatment of type 2 diabetes. A series of substituted 1,3-benzyl urea has been synthesized and evaluated for PTP1B inhibitory, antidiabetic and antidyslipidemic activities. The most active compound of the series 5b showed 79.4% PTP1B inhibition and 20.7% blood glucose lowering in the STZ model. It also lowered the serum cholesterol level by 16.3% and significantly increased the serum HDL-cholesterol by 46.8%. The high activity of compound 5b has been explained by docking studies. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).

Denmark, Scott E. et al. published their research in Journal of the American Chemical Society in 2014 | CAS: 14204-27-4

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

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).

Li, Yueshan et al. published their research in Journal of Medicinal Chemistry in 2022 | CAS: 754214-56-7

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

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).

Huang, Xi et al. published their research in RSC Advances in 2019 | CAS: 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

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).

Fujita, Hiroshi et al. published their research in Chemical & Pharmaceutical Bulletin in 1975 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 2-Phenylisoindolin-1-one

Synthetic studies on 2,4-benzothiazepin-5(1H)-one and 2,4-benzodiazepin-1-one derivatives was written by Fujita, Hiroshi;Sato, Yasunobu. And the article was included in Chemical & Pharmaceutical Bulletin in 1975.Name: 2-Phenylisoindolin-1-one This article mentions the following:

2,4-Benzothiazepin-5(1H)-ones were usually the predominant products in reactions of o-chloromethylbenzoyl chloride with 1,3-disubstituted thioureas; but with methyl, benzyl or allyl substituted thioureas, 2,4-benzodiazepin-1-ones were obtained together with 2,4-benzothiazepin-5(1H)-ones. These structures were elucidated from NMR spectra. The nature of the base and solvent as well as thiourea substituents affected the course of the reactions affording 2,4-benzothiazepin-5(1H)-ones or 2,4-benzodiazepin-1-ones. Several 2,4-benzothiazepin-5(1H)-ones and 2,4-benzodiazepin-1-ones possessed weak pharmacological activities, such as coronary vasodilating and local anesthetic activity. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

Reddy, Yervala D. et al. published their research in Letters in Organic Chemistry in 2013 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of Formula: C8HBr4NO2

A facile and green synthesis of novel imide and amidic acid derivatives of phenacetin as potential analgesic and anti-pyretic agents was written by Reddy, Yervala D.;Kumar, Padam P.;Devi, Bhoomireddy R.;Dubey, Pramod K.;Kumari, Yalamanchili B.. And the article was included in Letters in Organic Chemistry in 2013.COA of Formula: C8HBr4NO2 This article mentions the following:

Facile and green syntheses of potential analgesic and antipyretic compounds, N-(4-ethoxyphenyl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)acetamide derivatives and N-[(4-ethoxyphenylcarbamoyl)methyl]phthalamic acid derivatives have been developed. Two synthetic routes (A and B) have been established for the preparation of the former. In the route-A, 4-ethoxyaniline was reacted with chloroacetyl chloride in a solution of potassium acetate and acetic acid to yield N-(4-ethoxyphenyl)-2-chloroacetamide. The latter was reacted with imide compounds either in triethanolamine as a green solvent or in solid phase in the presence of TEBAC and KI to yield the products. Alternatively, in the route-B, reaction of anhydrides with glycine yielded the (1,3-dioxo-1,3-dihydroisoindol-2-yl)acetic acid derivatives which on reaction with 4-ethoxyaniline either in triethnolamine and DCC as a dehydrating agent or in solid phase in the presence of DCC gave the products. The latter were hydrolyzed in 0.5N ethanolic KOH to afford N-[(4-ethoxyphenylcarbamoyl)methyl]phthalamic acid derivatives In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7COA of Formula: C8HBr4NO2).

Tsuritani, Takayuki et al. published their research in Synlett in 2006 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Reference of 5388-42-1

A short and efficient synthesis of isoindolin-1-ones was written by Tsuritani, Takayuki;Kii, Satoshi;Akao, Atsushi;Sato, Kimihiko;Nonoyama, Nobuaki;Mase, Toshiaki;Yasuda, Nobuyoshi. And the article was included in Synlett in 2006.Reference of 5388-42-1 This article mentions the following:

A short and efficient synthesis of isoindolin-1-ones is reported. Base-induced cyclization of ortho-(hydroxymethyl)benzamides, which were easily prepared from the corresponding phthalides and amines, led predominantly to N-alkylation in good yield. The reaction proceeded under mild conditions and bromine and nitrile substituents were tolerated. The selectivity is explained by HASB theory. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Reference of 5388-42-1