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Zhang, Chufeng et al. published their research in European Journal of Medicinal Chemistry in 2019 | 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.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: C13H17BN2O2

Design, synthesis and evaluation of novel 7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives as potent, selective and reversible Bruton’s tyrosine kinase (BTK) inhibitors for the treatment of rheumatoid arthritis was written by Zhang, Chufeng;Pei, Heying;He, Jun;Zhu, Jiali;Li, Weimin;Niu, Ting;Xiang, Mingli;Chen, Lijuan. And the article was included in European Journal of Medicinal Chemistry in 2019.COA of Formula: C13H17BN2O2 This article mentions the following:

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives was designed and synthesized as reversible BTK inhibitors, and evaluated for their kinase selectivity, anti-proliferative activity against the B-cell lymphoma cell lines (Ramos, Jeko-1) and cell line BTK enhanced (Daudi) in vitro. Among them, pyrrolo[2,3-d]pyrimidine I exhibited the most excellent potency (IC₅₀ = 3.0 nM against BTK enzyme, 8.52 μM, 11.10 μM and 7.04 μM against Ramos, Jeko-1, Daudi cells, resp.), good kinase selectivity and inhibited BTK Y223 auto-phosphorylation and PLCγ2 Tyr1217 phosphorylation. Importantly, the compound I showed effective anti-arthritic effect on collagen-induced arthritis (CIA) model in vivo. 60 Mg/kg dose level once a day group displayed markedly reduced joint damage and cellular infiltration without any bone and cartilage morphol. change. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7COA of Formula: C13H17BN2O2).

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

DeRatt, Lindsey G. et al. published their research in Organic Letters in 2019 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.COA of Formula: C9H6BrNO2

Mild Intramolecular Ring Opening of Oxetanes was written by DeRatt, Lindsey G.;Lawson, Edward C.;Wang, Chao-Yuan;Kuduk, Scott D.. And the article was included in Organic Letters in 2019.COA of Formula: C9H6BrNO2 This article mentions the following:

Herein, an intramol. ring opening of oxetane carboxamides with mild nucleophiles, such as nitrogen heterocycles, is presented. The reaction proceeds under metal-free basic conditions which is highly unusual in ring opening reactions of oxetanes. Amide formation and oxetane ring opening/cyclization in a one-pot approach affords high levels of mol. complexity in a single step from simple, readily available substrates. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2COA of Formula: C9H6BrNO2).

Russell, Glen A. et al. published their research in Journal of the American Chemical Society in 1997 | CAS: 14204-27-4

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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Safety of 2-(Phenylthio)isoindoline-1,3-dione

Homolytic Base-Promoted Aromatic Alkylations by Alkylmercury Halides was written by Russell, Glen A.;Chen, Ping;Kim, Byeong Hyo;Rajaratnam, Ragine. And the article was included in Journal of the American Chemical Society in 1997.Safety of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Electron transfer chain reactions leading to substitution in electronegatively substituted benzene derivatives can be observed with alkylmercury halides in the presence of proton acceptors such as DABCO. Promotion by base involves the abstraction of a proton from the substituted cyclohexadienyl adduct radical to form a radical anion which readily transfers an electron to RHgX with the regeneration of Râ? Aromatic substitutions involving Me₃Câ?are highly regioselective and yield products of only para attack for PhCHO, PhCOMe, PhCOCMe₃, PhCOPh, PhCN, phthalimides, or 1,2-dicyanobenzene. The ortho/para substitution products are observed for isophthalaldehyde or 1,3-dicyanobenzene, while 1,4-dicyanobenzene yields the ortho substitution product. At 25-35Â° substitution by Me₃Câ?ortho to an ester group is not observed and m- or p-cyanobenzoate esters yield only products of substitution ortho to the cyano group. With Me₂CHâ?substitution ortho to the ester function is observed with di-Et isophthalate. Intramol. radical cyclizations of the radical adducts of 1-aryl-4-penten-1-ones leading to Î±-tetralones is also promoted by the presence of DABCO. When the aryl group contains a para ester function, spirocyclization occurs leading to a rearrangement acyl radical which can be oxidized by Me₃CHgCl to the acyl cation and the carboxylic acid. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Safety of 2-(Phenylthio)isoindoline-1,3-dione).

Yamamoto, Iwao et al. published their research in Tetrahedron Letters in 1971 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Computed Properties of C14H11NO

Reaction of isocyanate with phthalaldehyde was written by Yamamoto, Iwao;Tabo, Yoshizo;Gotoh, Haruo;Minami, Toru;Ohshiro, Yoshiki;Agawa, Toshio. And the article was included in Tetrahedron Letters in 1971.Computed Properties of C14H11NO This article mentions the following:

Phthalimidines (I) are prepared by the reaction of phthalaldehyde (II) with aryl isocyanates ArNCO. Thus, an equimolar mixture of PhNCO and II is heated to give N-phthalimidine (III). Similarly prepared are I (Ar = o-tolyl, m-ClC6H4, o-ClC6H4). Probably, IV are intermediates. II is treated with PhN:C:NPh to give III. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Computed Properties of C14H11NO).

Proctor, G. R. et al. published their research in Journal of the Chemical Society in 1972 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.SDS of cas: 5388-42-1

Azocine derivatives. I. Synthesis of 1-benzazocin-6-one derivatives by direct cyclization was written by Proctor, G. R.;Ross, W. I.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1972.SDS of cas: 5388-42-1 This article mentions the following:

Treatment of o-MeO2CC6H4NHSO2C6H4Me-p with Br(CH2)4CO2Et followed by NaH in DMF gave Et 1,2,3,4,5, 6-hexahydro-6-oxo-N-(p-tolylsulfonyl)-1-benzazocine-5-carboxylate (I, R = CO2Et) by Dieckmann cyclization. Acid hydrolysis of I (R = CO2Et) gave 2,3,4,6-tetrahydro-N-(p-tolylsulfonyl)-1-benzazocin-6(1H)-one (I, R = H) in 30% overall yield. NaBH4 reduction of I (R = H) gave the corresponding alc., which with Na-liquid NH3 gave 1,2,3,4,5,6-hexahydro-1-benzazocin-6-ol. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

Singha Roy, Soumya Jyoti et al. published their research in Organic & Biomolecular Chemistry in 2017 | 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.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 C14H9NO2S

“On water” catalytic enantioselective sulfenylation of deconjugated butyrolactams was written by Singha Roy, Soumya Jyoti;Mukherjee, Santanu. And the article was included in Organic & Biomolecular Chemistry in 2017.Computed Properties of C14H9NO2S This article mentions the following:

In the presence of phthalazine-linked quinidine or quinine dimers, deconjugated γ-butenolactams such as racemic I (R = H) underwent enantioselective arylsulfenylation and phenylselenenylation reactions with arylthio- and phenylselenosuccinimides in tert-butylbenzene/water mixtures to yield nonracemic α-arylthio- and α-phenylselenenobutenolactams such as I (R = PhS, PhSe) in 56-94% yields and in 47->96% ee; a lactam with an α-iso-Pr substituent and benzylthiol- and cyclohexanethiol-derived succinimides did not yield sulfenylation products. Oxidation and rearrangement of I (R = PhSe) yielded a nonracemic γ-hydroxybutenolactam by formal γ-hydroxylation; the selenylation and hydroxylation reactions were performed in tandem. The structures of I (R = PhS, PhSe) and of the oxidation and rearrangement product of I (R = PhSe) were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Computed Properties of C14H9NO2S).

Mussari, Christopher P. et al. published their research in ACS Medicinal Chemistry Letters in 2020 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C9H5BrN2

Discovery of Potent and Orally Bioavailable Small Molecule Antagonists of Toll-like Receptors 7/8/9 (TLR7/8/9) was written by Mussari, Christopher P.;Dodd, Dharmpal S.;Sreekantha, Ratna Kumar;Pasunoori, Laxman;Wan, Honghe;Posy, Shana L.;Critton, David;Ruepp, Stefan;Subramanian, Murali;Watson, Andrew;Davies, Paul;Schieven, Gary L.;Salter-Cid, Luisa M.;Srivastava, Ratika;Tagore, Debarati Mazumder;Dudhgaonkar, Shailesh;Poss, Michael A.;Carter, Percy H.;Dyckman, Alaric J.. And the article was included in ACS Medicinal Chemistry Letters in 2020.Formula: C9H5BrN2 This article mentions the following:

The toll-like receptor (TLR) family is an evolutionarily conserved component of the innate immune system, responsible for the early detection of foreign or endogenous threat signals. In the context of autoimmunity, the unintended recognition of self-motifs as foreign promotes initiation or propagation of disease. Overactivation of TLR7 and TLR9 have been implicated as factors contributing to autoimmune disorders such as psoriasis, arthritis, and lupus. In our search for small mol. antagonists of TLR7/9, 7f(I) was identified as possessing excellent on-target potency for human TLR7/9 as well as for TLR8, with selectivity against other representative TLR family members. Good pharmacokinetic properties and a relatively balanced potency against TLR7 and TLR9 in mouse systems (systems which lack functional TLR8) made this an excellent in vivo tool compound, and efficacy from oral dosing in preclin. models of autoimmune disease was demonstrated. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Formula: C9H5BrN2).

Gao, Shang et al. published their research in Organic & Biomolecular Chemistry in 2016 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 4583-55-5

Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction: approach to thiazole-fused pyrrolidinones with a C2-azaquarternary center was written by Gao, Shang;Yang, Chi;Huang, Yue;Zhao, Lei;Wu, Xiaoming;Yao, Hequan;Lin, Aijun. And the article was included in Organic & Biomolecular Chemistry in 2016.Product Details of 4583-55-5 This article mentions the following:

A Pd(II)-catalyzed intramol. oxidative Heck dearomative reaction for the construction of thiazole-fused pyrrolidinones with a C2-azaquarternary center and C3-exo-double bond has been achieved for the first time. The reaction exhibited good functional group tolerance and gram-scale capacity. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Product Details of 4583-55-5).

Zhao, Fei et al. published their research in Bioorganic & Medicinal Chemistry in 2016 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Related Products of 754214-56-7

Discovery and optimization of a series of imidazo[4,5-b]pyrazine derivatives as highly potent and exquisitely selective inhibitors of the mesenchymal-epithelial transition factor (c-Met) protein kinase was written by Zhao, Fei;Zhang, Jing;Zhang, Leduo;Hao, Yu;Shi, Chen;Xia, Guangxin;Yu, Jianxin;Liu, Yanjun. And the article was included in Bioorganic & Medicinal Chemistry in 2016.Related Products of 754214-56-7 This article mentions the following:

Aberrant c-Met activation has been implicated in multiple tumor oncogenic processes and drug resistance. In this study, a series of imidazo[4,5-b]pyrazine derivatives was designed and synthesized, and their inhibitory activities were evaluated in vitro. Structure-activity relationship (SAR) was investigated systematically and docking anal. was performed to elucidate the binding mode, leading to the identification of the most promising compound 1D-2 (I) which exhibited significant inhibitory effect on both enzymic (IC₅₀ = 1.45 nM) and cellular (IC₅₀ = 24.7 nM in H1993 cell line) assays, as well as exquisite selectivity and satisfactory metabolic stability in human and rat liver microsomes. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Related Products of 754214-56-7).

Joule, J. A. et al. published their research in Science of Synthesis in 2001 | CAS: 16732-64-2

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

Product class 13: indole and its derivatives was written by Joule, J. A.. And the article was included in Science of Synthesis in 2001.Reference of 16732-64-2 This article mentions the following:

A review of preparation of indoles and its derivatives Covered reactions include cyclization, ring transformation, aromatization and substituent modifications. Subclasses covered include 1H-indol-1-ols, 1,3-dihydro-2H-indol-2-ones, and 1,2-dihydro-3H-indol-3-ones. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Reference of 16732-64-2).