20/02/2023 - Page 13 of 14 - Indole Building Blocks

Niemeyer, Zachary L. et al. published their research in Journal of the American Chemical Society in 2017 | CAS: 89245-41-0

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 4-Bromoindole-3-acetic Acid

Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization was written by Niemeyer, Zachary L.;Pindi, Suresh;Khrakovsky, Dimitri A.;Kuzniewski, Christian N.;Hong, Cynthia M.;Joyce, Leo A.;Sigman, Matthew S.;Toste, F. Dean. And the article was included in Journal of the American Chemical Society in 2017.Safety of 4-Bromoindole-3-acetic Acid This article mentions the following:

Computed descriptors for acyclic diaminocarbene ligands are developed in the context of a gold catalyzed enantioselective tandem [3,3]-sigmatropic rearrangement-[2+2]-cyclization. Surrogate structures enable the rapid identification of parameters that reveal mechanistic characteristics. The observed selectivity trends are validated in a robust multivariate anal. facilitating the development of a highly enantioselective process. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Safety of 4-Bromoindole-3-acetic Acid).

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Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Shriver, James A. et al. published their research in RSC Advances in 2020 | 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate was written by Shriver, James A.;Wang, Katelyn R.;Patterson, Andrew C.;DeYoung, James R.;Lipsius, Richard J.. And the article was included in RSC Advances in 2020.Category: indole-building-block This article mentions the following:

Two independent methods generating 7-azaindoxyl as an intermediate verified that 7,7′-diazaindirubin was formed exclusively over 7,7′-diazaindigo. This contrasted with long-standing knowledge related to the reactivity of indoxyl, which proceeded via a radical-initiated homodimerization process, leading to indigo. A series of experiments confirmed 7-azaindoxyl as an intermediate with resulted suggesting a condensation pathway followed by oxidation In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Category: indole-building-block).

Soni, Love Kumar et al. published their research in International Journal of ChemTech Research in 2012 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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.Recommanded Product: 1912-45-4

Classical QSAR modelling of Indole-3-acetic acids for cancer therapy was written by Soni, Love Kumar. And the article was included in International Journal of ChemTech Research in 2012.Recommanded Product: 1912-45-4 This article mentions the following:

A set of 26 compound of the series halogenated Indole-3-acetic acids as oxidatively activate prodrugs with potential for targeted cancer therapy were subjected to quant. structure activity relationship (QSAR) anal. using combination of various electronic, thermodn. and spatial descriptors. Several statistical regression equations were obtained using multiple regression anal. QSAR anal. showed that the cytotoxin produced from oxidation of IAA with horseradish peroxidase (HRP) have significant correlation with electronic (Energy of Highest MO), and thermodn. (Non-1, 4-VDW energy, Henry law constant) properties of the mol. QSAR anal. suggests that substitution with electron withdrawing and bulkier group is more favorable for inhibitory activity. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Recommanded Product: 1912-45-4).

Das, Priyabrata et al. published their research in ACS Medicinal Chemistry Letters in 2013 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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.Formula: C8H3F2NO2

SAR-Based Optimization of a 4-Quinoline Carboxylic Acid Analogue with Potent Antiviral Activity was written by Das, Priyabrata;Deng, Xiaoyi;Zhang, Liang;Roth, Michael G.;Fontoura, Beatriz M. A.;Phillips, Margaret A.;De Brabander, Jef K.. And the article was included in ACS Medicinal Chemistry Letters in 2013.Formula: C8H3F2NO2 This article mentions the following:

It is established that drugs targeting viral proteins are at risk of generating resistant strains. However, drugs targeting host factors can potentially avoid this problem. Herein, we report structure-activity relationship studies leading to the discovery of a very potent lead compound 6-fluoro-2-(5-isopropyl-2-methyl-4-phenoxyphenyl)quinoline-4-carboxylic acid (C44) that inhibits human dihydroorotate dehydrogenase (DHODH) with an IC₅₀ of 1 nM and viral replication of VSV and WSN-Influenza with an EC₅₀ of 2 nM and 41 nM. We also solved the X-ray structure of human DHODH bound to C44, providing structural insight into the potent inhibition of biaryl ether analogs of brequinar. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Formula: C8H3F2NO2).

Barr, Rita et al. published their research in Proceedings of the Indiana Academy of Science in 1991 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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.Synthetic Route of C10H8ClNO2

The effect of chloro-derivatives of indoleacetic acid on plasma membrane electron transport and proton excretion was written by Barr, Rita;Boettger, Michael;Crane, Frederick L.. And the article was included in Proceedings of the Indiana Academy of Science in 1991.Synthetic Route of C10H8ClNO2 This article mentions the following:

As shown by M. Boettger and H. Hilgendorf (1988), the natural auxin indoleacetic acid in high concentrations (10 濠电偞鎸鹃幏? inhibited both e^– and proton efflux by corn roots of undamaged plants measured with a pH-stat combined with a redoxstat. In this study, it is shown that of various chloro-substituted indoleacetic acid derivatives, only 4-chloro-IAA inhibited NADH oxidation and several derivatives stimulated trans-membrane hexacyanoferrate reduction in concentrations from 0.1 nM to 10 濠电偞鎸鹃幏?in cultured carrot cells. Proton excretion by these cells was also stimulated by 5-, 6- and 5,7-chloro substituted indoleacetic acid, but the 4-chloro derivative inhibited H⁺ excretion by the plasma membrane H⁺-ATPase, while H⁺ excretion in presence of hexacyanoferrate was stimulated. These divergent effects of chloro-substituted indoleacetic acid derivatives show that the trans-membrane redox system is not directly related to proton movement through the membrane in a 1:1 relationship. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Synthetic Route of C10H8ClNO2).

Polamo, M. et al. published their research in Zeitschrift fuer Kristallographie – New Crystal Structures in 2003 | 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.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

Crystal structure of 4-N-phenylisoindolinone, C₁₄H₁₁NO was written by Polamo, M.;Talja, M.. And the article was included in Zeitschrift fuer Kristallographie – New Crystal Structures in 2003.SDS of cas: 5388-42-1 This article mentions the following:

The title compound is monoclinic, space group P2₁/n, a 5.925(4), b 7.556(2), c 23.11(1) 闂? 闁?94.67(5)闂? Z = 4, Rgt(F) = 0.055, wRref(F²) = 0.140, T = 193 K. At. coordinates are given. The title compound, 4-N-phenylisoindolinone, has a slightly distorted sp2-hybridized nitrogen, the sum of angles at N1 is 359.1闂? Since the Ph ring is almost coplanar to the isoindolinone plane, 9.4(1)闂? a reasonable 闂?interaction could be expected. The bond length of N1-C1 is slightly shorter, 1.421(3) 闂? than in 2-[2,6-bis(1-methylethyl)phenyl]-2,3-dihydro-1H-isoindol-1-one, 1.428(2) 闂? in which 闂?interaction can not exist because the aryl ring adopts perpendicular orientation to the isoindolinone part of the mol. The 闂?interaction of the nitrogen to the Ph ring might also explain the weaker interaction of the nitrogen to the carbonyl group; N1-C2 bond is 1.376(3) 闂? whereas in 2-[2,6-bis(1-methylethyl)phenyl]-2,3-dihydro-1H-isoindol-1-one bond length is 1.358(2) 闂? In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

Harrison, William T. A. et al. published their research in Acta Crystallographica, Section E: Structure Reports Online in 2006 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 167631-84-7

5-Fluoro-1H-indole-2-carbohydrazide was written by Harrison, William T. A.;Yathirajan, H. S.;Ashalatha, B. V.;Raj, K. K. Vijaya;Narayana, B.. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2006.Related Products of 167631-84-7 This article mentions the following:

The geometric parameters for the essentially planar mol. of the title compound, C₉H₈FN₃O, are normal. A network of N-H…O and N-H…N H-bonds helps to establish the crystal packing. Crystal data: orthorhombic, space group Pbca, a 10.0451(3), b 9.4978(2), c 18.5293(6) 闂? Z = 8, d = 1.452 g/cm, 1497 observed reflections with I > 2(I), 140 refined parameters, R[F² > 2闂?F²)] = 0.032, wR(F²) = 0.089. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Related Products of 167631-84-7).

Tilley, Jefferson W. et al. published their research in Journal of Medicinal Chemistry in 1980 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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. 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). Product Details of 150560-58-0

Pyrido[2,1-b]quinazolinecarboxylic acids as orally active antiallergy agents was written by Tilley, Jefferson W.;LeMahieu, Ronald A.;Carson, Mathew;Kierstead, Richard W.;Baruth, Herman W.;Yaremko, Bohdan. And the article was included in Journal of Medicinal Chemistry in 1980.Product Details of 150560-58-0 This article mentions the following:

Eight title compounds I (R = CO₂H, H, Me, or CHMe₂; R¹ = H, Me, CHMe₂, Ac, N(:CMe)OMe, or CO₂H) were synthesized by the Ni carbonyl mediated carboxylation of the corresponding bromides. Comparable antiallergy activities were observed for both the 2-alkyl-8-carboxy and the corresponding 8-alkyl-2-carboxy analogs. I; R = CO₂H, R¹ = CHMe₂ [68700-95-8] was one of the most active substances administered orally in the rat passive cutaneous anaphylasis test. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Product Details of 150560-58-0).

Wen, Wuqiang et al. published their research in Journal of Medicinal Chemistry in 2022 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 5388-42-1

Structure-Guided Discovery of the Novel Covalent Allosteric Site and Covalent Inhibitors of Fructose-1,6-Bisphosphate Aldolase to Overcome the Azole Resistance of Candidiasis was written by Wen, Wuqiang;Cao, Hongxuan;Huang, Yunyuan;Tu, Jie;Wan, Chen;Wan, Jian;Han, Xinya;Chen, Han;Liu, Jiaqi;Rao, Li;Su, Chen;Peng, Chao;Sheng, Chunquan;Ren, Yanliang. And the article was included in Journal of Medicinal Chemistry in 2022.Related Products of 5388-42-1 This article mentions the following:

Fructose-1,6-bisphosphate aldolase (FBA) represents an attractive new antifungal target. Here, we employed a structure-based optimization strategy to discover a novel covalent binding site (C292 site) and the first-in-class covalent allosteric inhibitors of FBA from Candida albicans (CaFBA). Site-directed mutagenesis, liquid chromatog.-mass spectrometry, and the crystallog. structures of APO-CaFBA, CaFBA-G3P, and C157S-I revealed that S268 is an essential pharmacophore for the catalytic activity of CaFBA, and L288 is an allosteric regulation switch for CaFBA. Furthermore, most of the CaFBA covalent inhibitors exhibited good inhibitory activity against azole-resistant C. albicans, and compound II can inhibit the growth of azole-resistant strains 103 with the MIC₈₀ of 1濠电偞鎸鹃幐?mL. Collectively, this work identifies a new covalent allosteric site of CaFBA and discovers the first generation of covalent inhibitors for fungal FBA with potent inhibitory activity against resistant fungi, establishing a structural foundation and providing a promising strategy for the design of potent antifungal drugs. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Related Products of 5388-42-1).

Zhang, Ming-Zhi et al. published their research in Tetrahedron in 2021 | 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 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: 827-01-0

First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents was written by Zhang, Ming-Zhi;Mulholland, Nick;Seville, Anne;Hough, Gemma;Smith, Nicholas;Dong, Hong-Qiang;Zhang, Wei-Hua;Gu, Yu-Cheng. And the article was included in Tetrahedron in 2021.SDS of cas: 827-01-0 This article mentions the following:

Pimprinine and streptochlorin are indole natural products produced by many species of organisms, and they are reported to possess a wide range of biol. activities, such as anticancer, antiviral, antifungal activity and so on. In this study, three series of pimprinine derivatives or analogs were efficiently synthesized under the optimized methods. Biol. assays conducted at Syngenta firstly indicated the pimprinine derivatives or analogs possessed potential herbicidal and insecticidal activity, and this is highlighted by several compounds that possessed significant biol. activity as well as broad spectrum. Meanwhile, compounds with benzothiophene-oxazole core showed effective nematicidal activity in primary screening. Compounds 5-(benzofuran-3-yl)oxazole and 5-(benzodioxol-5-yl)oxazole were identified as the most promising lead structures for further study. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0SDS of cas: 827-01-0).