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Jiang, Zhi et al. published their research in Organic & Biomolecular Chemistry in 2022 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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.Computed Properties of C9H6BrNO2

Palladium oxidative addition complex-enabled synthesis of amino-substituted indolyl-4(3H)-quinazolinones and their antitumor activity evaluation was written by Jiang, Zhi;Zhao, Dan-Dan;Hu, Yu-Tao;Rao, Yong;Guo, Shi-Yao;Xu, Yao-Hao;Li, Qingjiang;Huang, Zhi-Shu. And the article was included in Organic & Biomolecular Chemistry in 2022.Computed Properties of C9H6BrNO2 This article mentions the following:

A palladium-mediated amination of halogen-containing indolyl-4(3H)-quinazolinones such as I (R = Br) with a variety of primary and secondary amines, e.g., morpholine via the corresponding palladium oxidative addition complexes was reported. The protocol allows the facile synthesis of indolyl-4(3H)-quinazolinone derivatives with amino groups at all the positions of the benzene ring such as I (R = 4-morpholinyl) in moderate to good yields with mild reaction conditions and good functional group tolerance. Furthermore, the antitumor activity of these products was evaluated. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Computed Properties of C9H6BrNO2).

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

Geng, Kaijun et al. published their research in Organic Chemistry Frontiers in 2016 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 2-Phenylisoindolin-1-one

Rhodium-catalyzed oxidative coupling of N-acyl anilines with alkynes using an acylamino moiety as the traceless directing group was written by Geng, Kaijun;Fan, Zhoulong;Zhang, Ao. And the article was included in Organic Chemistry Frontiers in 2016.Recommanded Product: 2-Phenylisoindolin-1-one This article mentions the following:

A rhodium-catalyzed oxidative annulation of N-acyl anilines with alkynes was developed by using the acylamino group as a traceless directing group for the first time. Various N-acyl anilines and para- or meta-substituted diphenylacetylenes were well tolerated, and a series of 1,2,3,4-tetrasubstituted naphthalenes were readily synthesized in good to excellent yields. Meanwhile, this method also provided a new strategy for the N-dearylation of N-phenylamides. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 2-Phenylisoindolin-1-one).

Goodfellow, Val S. et al. published their research in Journal of Medicinal Chemistry in 2013 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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. 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.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester

Discovery, Synthesis, and Characterization of an Orally Bioavailable, Brain Penetrant Inhibitor of Mixed Lineage Kinase 3 was written by Goodfellow, Val S.;Loweth, Colin J.;Ravula, Satheesh B.;Wiemann, Torsten;Nguyen, Thong;Xu, Yang;Todd, Daniel E.;Sheppard, David;Pollack, Scott;Polesskaya, Oksana;Marker, Daniel F.;Dewhurst, Stephen;Gelbard, Harris A.. And the article was included in Journal of Medicinal Chemistry in 2013.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

Inhibition of mixed lineage kinase 3 (MLK3) is a potential strategy for treatment of Parkinson’s disease and HIV-1 associated neurocognitive disorders (HAND), requiring an inhibitor that can achieve significant brain concentration levels. We report here URMC-099 (1) an orally bioavailable (F = 41%), potent (IC₅₀ = 14 nM) MLK3 inhibitor with excellent brain exposure in mouse PK models and minimal interference with key human CYP450 enzymes or hERG channels. The compound inhibits LPS-induced TNFα release in microglial cells, HIV-1 Tat-induced release of cytokines in human monocytes and up-regulation of phospho-JNK in Tat-injected brains of mice. Compound 1 likely functions in HAND preclin. models by inhibiting multiple kinase pathways, including MLK3 and LRRK2 (IC₅₀ = 11 nM). We compare the kinase specificity and BBB penetration of 1 with CEP-1347 (2). Compound 1 is well tolerated, with excellent in vivo activity in HAND models, and is under investigation for further development. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

Klose, Jana et al. published their research in Tetrahedron in 1997 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: C14H9NO2S

Preparation of 2-[(2-cyanoethyl)thio]-1H-isoindole-1,3(2H)-dione and related sulfur-transfer agents was written by Klose, Jana;Reese, Colin B.;Song, Quanial. And the article was included in Tetrahedron in 1997.Formula: C14H9NO2S This article mentions the following:

The title compound (I, R = CH₂CH₂CN) and a morpholine analog (II) are both conveniently prepared in good yield from 2-cyanoethyl disulfide, which itself is readily prepared in one step from S-(2-cyanoethyl)isothiouronium chloride. In the same way, di-Me and di-Ph disulfides are converted to I (R = Me, Ph, resp.), also in good yields. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Wang, Dawei et al. published their research in Synlett in 2016 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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.Safety of 4-Bromo-1H-indole-2-carboxylic acid

Transition-Metal-Free Direct Arylation and Esterification Reaction of Unprotected Indolylcarboxylic Acid Derivatives: A New Entry to 2-(1H-Indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazole and Aryl 1H-Indole-2-carboxylates was written by Wang, Dawei;Ge, Chenyang;Yu, Xin;Wan, Huida;Xu, Xiang. And the article was included in Synlett in 2016.Safety of 4-Bromo-1H-indole-2-carboxylic acid This article mentions the following:

An efficient, ligand-free, transition-metal-free, direct arylation and esterification reaction of unprotected indolylcarboxylic acid derivatives with diaryliodonium salts was developed, thus providing a new entry to 2-(1H-indol-2-yl)-5-(phenylthio)-1,3,4-oxadiazole and aryl 1H-indole-2-carboxylate derivatives I (R = H, 4-MeO, 4-F, 5-NO₂, 4-Br; Ar = Ph, 4-MeC₆H₄) with good yields. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Safety of 4-Bromo-1H-indole-2-carboxylic acid).

Jablonowski, Jill A. et al. published their research in Journal of Medicinal Chemistry in 2003 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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 In Synthesis of 4-Bromo-1H-indole-2-carboxylic acid

The First Potent and Selective Non-Imidazole Human Histamine H₄ Receptor Antagonists was written by Jablonowski, Jill A.;Grice, Cheryl A.;Chai, Wenying;Dvorak, Curt A.;Venable, Jennifer D.;Kwok, Annette K.;Ly, Kiev S.;Wei, Jianmei;Baker, Sherry M.;Desai, Pragyna J.;Jiang, Wen;Wilson, Sandy J.;Thurmond, Robin L.;Karlsson, Lars;Edwards, James P.;Lovenberg, Timothy W.;Carruthers, Nicholas I.. And the article was included in Journal of Medicinal Chemistry in 2003.Application In Synthesis of 4-Bromo-1H-indole-2-carboxylic acid This article mentions the following:

Following the discovery of the human histamine H₄ receptor, a high throughput screen of our corporate compound collection identified a potential lead compound Investigation of the structure-activity relationship (SAR) resulted in the discovery of novel compounds, which are the first potent and selective histamine H₄ receptor antagonists to be described. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Application In Synthesis of 4-Bromo-1H-indole-2-carboxylic acid).

Jia, Xue-Gong et al. published their research in Chemical Science in 2018 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. 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 In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols was written by Jia, Xue-Gong;Guo, Peng;Duan, Jicheng;Shu, Xing-Zhong. And the article was included in Chemical Science in 2018.Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

A general and practical strategy to address the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis is reported. This strategy is used for the coupling of aryl bromides R¹Br (R¹ = 4-MeO₂CC₆H₄, benzofuran-5-yl, indol-4-yl, etc.) with allylic alcs. R²CH:CHCR³R⁴OH (R² = H, Me, Ph, etc.; R³ = R⁴ = H, Me; R³ = Me, Et, Ph, R⁴ = H) to form linear allylarenes R¹CR³R⁴CH:CHR². The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcs., and various heterocycles) and works with various allylic alcs. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments revealed that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcs. in the presence of Mn. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate).

Yuan, Yu-Chao et al. published their research in Organic Letters in 2017 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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: 2-Phenylisoindolin-1-one

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives was written by Yuan, Yu-Chao;Kamaraj, Raghu;Bruneau, Christian;Labasque, Thierry;Roisnel, Thierry;Gramage-Doria, Rafael. And the article was included in Organic Letters in 2017.Name: 2-Phenylisoindolin-1-one This article mentions the following:

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO₂ release with water being the source of protons. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

Knorr, Gergely et al. published their research in Bioconjugate Chemistry in 2018 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Category: indole-building-block

Bioorthogonally Applicable Fluorogenic Cyanine-Tetrazines for No-Wash Super-Resolution Imaging was written by Knorr, Gergely;Kozma, Eszter;Schaart, Judith M.;Nemeth, Krisztina;Torok, Gyorgy;Kele, Peter. And the article was included in Bioconjugate Chemistry in 2018.Category: indole-building-block This article mentions the following:

The synthesis, fluorogenic characterization, and labeling application of four tetrazine-quenched cyanine probes with emission maxima in the red-far red range is reported. Fluorescence of the cyanine-cores is quenched via through-bond-energy-transfer (TBET) exerted by a bioorthogonal tetrazine unit. Upon bioorthogonal labeling reaction with cyclooctyne tagged proteins, the quenching effect ceases, and thus the fluorescence reinstates, resulting in an increase in fluorescence intensity. As a rare example among indocyanines, one of the new probes was found suitable in STED-based super-resolution imaging. The applicability of this fluorogenic Tet-Cy3 probe was therefore further demonstrated in the bioorthogonal labeling of cytoskeletal protein, actin, with subsequent super-resolution microscopy (STED) imaging even under no-wash conditions. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Category: indole-building-block).

Denmark, Scott E. et al. published their research in Journal of Organic Chemistry in 2017 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Electric Literature of C14H9NO2S

Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines was written by Denmark, Scott E.;Chi, Hyung Min. And the article was included in Journal of Organic Chemistry in 2017.Electric Literature of C14H9NO2S This article mentions the following:

A method for the catalytic, enantioselective, intramol. sulfenoamination of alkenes with aniline nucleophiles has been developed. The method employs a chiral, Lewis basic selenophosphoramide catalyst and a Bronsted acid co-catalyst to promote stereocontrolled C-N and C-S bond formation by activation of an achiral sulfenylating agent. Benzoannulated nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, e.g., I, and tetrahydrobenzazepines were prepared with high to excellent enantioselectivities. The impact of tether length and electron d. of both the nucleophile and olefin on the reactivity, site selectivity, and enantioselectivity were investigated and interpreted in terms of substrate-dependent stereodetermining thiiranium ion formation or capture. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Electric Literature of C14H9NO2S).