05/01/2023 - Page 9 of 11 - Indole Building Blocks

Wang, Shuai et al. published their research in Organic Letters in 2019 | 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 827-01-0

N-Alkylation-Initiated Redox-Neutral [5 + 2] Annulation of 3-Alkylindoles with o-Aminobenzaldehydes: Access to Indole-1,2-Fused 1,4-Benzodiazepines was written by Wang, Shuai;Shen, Yao-Bin;Li, Long-Fei;Qiu, Bin;Yu, Liping;Liu, Qing;Xiao, Jian. And the article was included in Organic Letters in 2019.Related Products of 827-01-0 This article mentions the following:

An unprecedented N-alkylation-initiated redox-neutral [5 + 2] annulation of 3-alkylindoles I (R¹ = H, 4-F, 5-PhCH₂O, etc.; R² = Me, i-Pr, 3-indolylmethyl) with o-aminobenzaldehydes II [R³ = H, 3-Cl, 4-MeO, 5-Br, etc.; R⁴R⁵ = (CH₂)₃, (CH₂)₄, o-C₆H₄CH₂CH₂, etc.] via a cascade N-alkylation/dehydration/[1,5]-hydride transfer/Friedel-Crafts alkylation sequence is described. A series of indole-1,2-fused 1,4-benzodiazepines III was facilely constructed in moderate to good yields in one-step. This protocol features excellent regioselectivity, metal-free conditions, high step-economy and wide substrate scope. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Related Products of 827-01-0).

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

Bao, Xiaoze et al. published their research in Organic Letters in 2015 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. 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.Product Details of 14204-27-4

An Organocatalytic Asymmetric Friedel-Crafts Addition/Fluorination Sequence: Construction of Oxindole-Pyrazolone Conjugates Bearing Vicinal Tetrasubstituted Stereocenters was written by Bao, Xiaoze;Wang, Baomin;Cui, Longchen;Zhu, Guodong;He, Yuli;Qu, Jingping;Song, Yuming. And the article was included in Organic Letters in 2015.Product Details of 14204-27-4 This article mentions the following:

A highly efficient and practical one-pot sequential process, consisting of an organocatalytic enantioselective Friedel-Crafts-type addition of 4-nonsubstituted pyrazolones to isatin-derived N-Boc ketimines and a subsequent diastereoselective fluorination of the pyrazolone moiety, is developed. This reaction sequence delivers novel oxindole-pyrazolone adducts featuring vicinal tetrasubstituted stereocenters with a 0.5 mol % catalyst loading in high yield with excellent enantio- and diastereocontrol. Notably, chloro, bromo, and thioether functionalities can be readily incorporated, rendering a broad diversity of the product. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Product Details of 14204-27-4).

Sreenivasachary, Nampally et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2017 | CAS: 4769-96-4

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). Name: 6-Nitro-1H-indole

Discovery and characterization of novel indole and 7-azaindole derivatives as inhibitors of β-amyloid-42 aggregation for the treatment of Alzheimer’s disease was written by Sreenivasachary, Nampally;Kroth, Heiko;Benderitter, Pascal;Hamel, Anne;Varisco, Yvan;Hickman, David T.;Froestl, Wolfgang;Pfeifer, Andrea;Muhs, Andreas. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Name: 6-Nitro-1H-indole This article mentions the following:

The aggregation of amyloid-β peptides into cytotoxic oligomeric and fibrillary aggregates is believed to be one of the major pathol. events in Alzheimer disease. Here we report the design and synthesis of a novel series of indole and 7-azaindole derivatives containing, nitrile, piperidine and N-methyl-piperidine substituents at the 3-position to prevent the pathol. self-assembly of amyloid-β. We have further demonstrated that substitution of the azaindole and indole derivatives I (R = F, OMe) at the 3 positions is required to obtain compounds with improved physicochem. properties to allow brain penetration. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

Takahashi, Ichiro et al. published their research in Heterocycles in 2019 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.COA of Formula: C14H11NO

Exploration of moderate conditions and substrate variation in the direct condensation between phthalide and primary amine catalyzed by GaCl₃. Are aliphatic amines less reactive than aromatic ones? was written by Takahashi, Ichiro;Nishiwaki, Yoshinori;Saitoh, Kenta;Matsunaga, Takatoshi;Aratake, Akihiro;Morita, Toshio;Hosoi, Shinzo. And the article was included in Heterocycles in 2019.COA of Formula: C14H11NO This article mentions the following:

Direct condensation between phthalide and primary amines RNH₂ (R = n-Bu, 2-nitrophenyl, naphthalen-2-yl, etc.) in the presence of Lewis acid was achieved for the first time in organic solvent-diluted reaction systems catalyzed by GaCl₃. The peripheral aspect of this reaction is discussed. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1COA of Formula: C14H11NO).

Zhang, Shan-Jun et al. published their research in European Journal of Organic Chemistry in 2009 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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. 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.Computed Properties of C8HBr4NO2

Enantioselective Allylic Amination of Morita-Baylis-Hillman Carbonates Catalysed by Modified Cinchona Alkaloids was written by Zhang, Shan-Jun;Cui, Hai-Lei;Jiang, Kun;Li, Rui;Ding, Zhen-Yu;Chen, Ying-Chun. And the article was included in European Journal of Organic Chemistry in 2009.Computed Properties of C8HBr4NO2 This article mentions the following:

An efficient procedure for the asym. allylic amination of Morita-Baylis-Hillman carbonates I (R = Ph, 2-ClC₆H₄, 3-MeC₆H₄, 1-naphthyl, 2-thienyl, etc.) with cyclic imides II (phthalimide, tetrachlorophthalimide, tetrabromophthalimide, cis-hexahydrophthalimide, 1,8-naphthalimide) catalyzed by com. available cinchona alkaloids is reported. It proves to be a facile protocol that affords α-methylene-β-imido esters III with good-to-excellent enantioselectivities (up to 94 % ee) and in high yields (up to 97 %). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009). In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Computed Properties of C8HBr4NO2).

Smith, Steven et al. published their research in ACS Omega in 2017 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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 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). Formula: C13H17BN2O2

Characterization of Covalent-Reversible EGFR Inhibitors was written by Smith, Steven;Keul, Marina;Engel, Julian;Basu, Debjit;Eppmann, Simone;Rauh, Daniel. And the article was included in ACS Omega in 2017.Formula: C13H17BN2O2 This article mentions the following:

Within the spectrum of kinase inhibitors, covalent-reversible inhibitors (CRIs) provide a valuable alternative approach to classical covalent inhibitors. This special class of inhibitors can be optimized for an extended drug-target residence time. For CRIs, it was shown that the fast addition of thiols to electron-deficient olefins leads to a covalent bond that can break reversibly under proteolytic conditions. Research groups are just beginning to include CRIs in their arsenal of compound classes, and, with that, the understanding of this interesting set of chem. warheads is growing. However, systems to assess both characteristics of the covalent-reversible bond in a simple exptl. setting are sparse. Here, we have developed an efficient methodol. to characterize the covalent and reversible properties of CRIs and to investigate their potential in targeting clin. relevant variants of the receptor tyrosine kinase EGFR. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Formula: C13H17BN2O2).

Yang, Zhao et al. published their research in RSC Advances in 2016 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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.HPLC of Formula: 4769-96-4

Cu-catalyzed β-functionalization of saturated ketones with indoles: a one-step synthesis of C3-substituted indoles was written by Yang, Zhao;Liu, Chengkou;Zeng, Yu;Zhang, Jingming;Wang, Zhixiang;Fang, Zheng;Guo, Kai. And the article was included in RSC Advances in 2016.HPLC of Formula: 4769-96-4 This article mentions the following:

An effective one-pot synthesis of β-indolylketones I [R¹ = H, 4-Me, 4-F, etc.; R² = 2-Me, 5-CN, 6-NO², etc.] from saturated ketones and indoles was developed. It is noteworthy that this methodol. has a good functional group tolerance (alkyl, nitro, halogen, hydroxyl, methoxyl, carboxyl and ester) and is of great significance to the preparation of many indole heterocycles. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4HPLC of Formula: 4769-96-4).

Yu, Liangmin et al. published their research in Zhongguo Haiyang Daxue Xuebao, Ziran Kexueban in 2009 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Synthetic Route of C11H11NO2

Synthesis of 3-(indolyl)propanoic acid and its derivatives was written by Yu, Liangmin;Li, Xia;Yan, Xuefeng;Yu, Liangzhi. And the article was included in Zhongguo Haiyang Daxue Xuebao, Ziran Kexueban in 2009.Synthetic Route of C11H11NO2 This article mentions the following:

A method for the synthesis of the title compounds [i.e., 1H-indole-1-propanoic acid derivatives] is reported here. Reaction of indole derivatives with 3,3′-dithiobis[propanoic acid] di-Me ester gave 1H-indole-1-propanoic acid Me ester derivatives Saponification/hydrolysis of these intermediates and acidification delivered the target compounds (49.5%, 50.8%, 35.1% yield). Product structures were determined by IR and NMR. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Synthetic Route of C11H11NO2).

Adams, Sarah E. et al. published their research in MedChemComm in 2012 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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). HPLC of Formula: 827-01-0

Potent inhibition of Ca²⁺-dependent activation of calpain-1 by novel mercaptoacrylates was written by Adams, Sarah E.;Parr, Christian;Miller, David J.;Allemann, Rudolf K.;Hallett, Maurice B.. And the article was included in MedChemComm in 2012.HPLC of Formula: 827-01-0 This article mentions the following:

Calpain-1 is a Ca²⁺-activated cytosolic cysteine protease. Its activation has been linked to extravasation into inflamed tissue of white blood cells, especially neutrophils. Calpain-1 may therefore be an anti-inflammatory target for therapeutic intervention. 24 novel monohalogenated Ph and indole mercaptoacrylic acid derivatives were synthesized. The location and nature of the ring-coupled halides strongly influenced the potency of these compounds to inhibit calpain activation. Several of the calpain-1 inhibitors showed IC₅₀ values in the low nanomolar range and prevented cell shape change of neutrophils, a necessary prelude to their migration from the blood in the body. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0HPLC of Formula: 827-01-0).

Furukawa, Shinya et al. published their research in ACS Catalysis in 2014 | CAS: 4769-96-4

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 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). Application In Synthesis of 6-Nitro-1H-indole

Chemoselective Hydrogenation of Nitrostyrene to Aminostyrene over Pd- and Rh-Based Intermetallic Compounds was written by Furukawa, Shinya;Yoshida, Yurika;Komatsu, Takayuki. And the article was included in ACS Catalysis in 2014.Application In Synthesis of 6-Nitro-1H-indole This article mentions the following:

A noble catalytic system based on intermetallic compounds was developed for the chemoselective hydrogenation of p-nitrostyrene (NS) to p-aminostyrene (AS). The main concept of the catalyst design was to construct polar active sites consisting of two types of metals with different electronegativities. We prepared a series of Pd- and Rh-based intermetallics and investigated their catalytic properties in detail in the catalytic transfer hydrogenation of nitrobenzene and NS in the presence of 4-methyl-1-cyclohexene (MC) or methanol as a hydrogen donor. FT-IR studies of adsorbed CO confirmed that the number of Pd ensembles exposed on a surface was greatly decreased by the formation of an intermetallic phase; hence, the particle surface consisted of two metal elements being coadjacent at the at. level. The product distribution achieved with Pd catalysts was dependent on the electronegativity of the second metal element: more electroneg. metals gave higher AS selectivity and lower p-ethylnitrobenzene selectivity. Rh catalysts selectively gave AS, and their AS yields increased as the electronegativity of the second metal increased. The results revealed that an increase in the electronegativity of the second metal element provided polar sites and enhanced the activation of methanol as a hydrogen donor, which accelerated the hydrogenation of the nitro group of NS and, hence, improved the yield of AS. The high selectivity of Rh catalysts was due to the absence of MC activation ability, which caused the hydrogenation of the vinyl group of NS. Pd₁₃Pb₉ exhibited the highest chemoselectivity toward AS (92%) among the investigated Pd catalysts. Moreover, RhPb₂ exhibited not only high AS selectivity (93%) but also the highest NS conversion (94%) among the investigated catalysts. RhPb₂ also exhibited high selectivity toward AS (91%), even when H₂ was used as a hydrogen source. Thus, intermetallics that contain Pb, which was the most electroneg. metal used in this study, afforded good catalytic performance and were observed to be good catalysts for the chemoselective hydrogenation of NS. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Application In Synthesis of 6-Nitro-1H-indole).