Category: indole-building-block

Isoindoles from phthalimidines. N-Arylisoindoles was written by Kovtunenko, V. A.;Kucherenko, T. T.;Kornilov, M. Yu.;Tyltin, A. K.;Turov, A. V.;Babichev, F. S.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1987.Electric Literature of C14H11NO This article mentions the following:

N-Arylisoindoles I (R = Ph, 4-MeC₆H₄, 4-BrC₆H₄) were prepared by reduction of the resp. phthalimidines II (same R) with Li[(MeOCH₂CH₂O)₂AlH₂]. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).

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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Electric Literature of C14H11NO

Referemce:
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

Identification of Novel d-Amino Acid Oxidase Inhibitors by in Silico Screening and Their Functional Characterization in Vitro was written by Katane, Masumi;Osaka, Naoko;Matsuda, Satsuki;Maeda, Kazuhiro;Kawata, Tomonori;Saitoh, Yasuaki;Sekine, Masae;Furuchi, Takemitsu;Doi, Issei;Hirono, Shuichi;Homma, Hiroshi. And the article was included in Journal of Medicinal Chemistry in 2013.Application In Synthesis of 4-Bromo-1H-indole-2-carboxylic acid This article mentions the following:

D-Amino acid oxidase (DAO) is a degradative enzyme that is stereospecific for d-amino acids, including d-serine and d-alanine, which are potential coagonists of the N-methyl-d-aspartate (NMDA) receptor. Dysfunction of NMDA receptor-mediated neurotransmission has been implicated in the onset of various mental disorders such as schizophrenia. Hence, a DAO inhibitor that augments the brain levels of d-serine and/or d-alanine and thereby activates NMDA receptor function is expected to be an antipsychotic drug, for instance, in the treatment of schizophrenia. In the search for potent DAO inhibitor(s), a large number of compounds were screened in silico, and several compounds were estimated as candidates. These compounds were then characterized and evaluated as novel DAO inhibitors in vitro. The results reported in this study indicate that some of these compounds are possible lead compounds for the development of a clin. useful DAO inhibitor and have the potential to serve as active site probes to elucidate the structure-function relationships of DAO. 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).

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

Referemce:
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

Synthesis, cytotoxic, antioxidant and anti-inflammatory activity of 3-((3-((6-benzoyl-1H-benz [D]imidazol-2-YL) amino)-5-mercapto- 4H-1,2, 4-triazol-4-YL) imino)substituted indol-2-ones was written by Rani, B. Shoba;Blessi, Priyanka K.;Sammaiah, G.. And the article was included in American Journal of PharmTech Research in 2016.HPLC of Formula: 112656-95-8 This article mentions the following:

In the present study novel series of 3-((3-((6-benzoyl-1H-benz[d]imidazol-2-yl) amino)-5- mercapto-4H-1, 2, 4-triazol-4-yl)imino)substituted indolin-2-ones have been synthesized in good yields and characterized by IR, NMR and Mass spectral analyses. Compounds were evaluated for their preliminary in vitro cytotoxic activity against HCT-116 (colon), MCF-7 (breast), HeLa (cervical) and HepG2 (hepatocellular) cancer cell lines by standard MTT assay method, antioxidant activity by standard DPPH assay method and also were screened for in vitro antiinflammatory activity. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8HPLC of Formula: 112656-95-8).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.HPLC of Formula: 112656-95-8

Referemce:
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

Synthesis of a near-IR cyanine and its application in determination of biomolecules was written by Zheng, Hong;Li, Donghui;Chen, Qiuying;Xy, Jingou. And the article was included in Yingyong Huaxue in 1999.Product Details of 146368-07-2 This article mentions the following:

A novel water soluble near-IR cyanine dye (HMC) was synthesized and its structure was characterized by NMR and MS. The absorption and fluorescence spectral characteristics of HMC in aqueous solutions were also studied. It was found that in acidic solution of HMC the presence of protein could cause a hypochromic effect at 776 nm, that was used as a probe for the determination of total protein in human serum. The low fluorescence of in situ HMC dimer caused by cationic surfactant CTAB has been tested as a probe for nucleic acid determination In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Product Details of 146368-07-2).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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.Product Details of 146368-07-2

Referemce:
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

Carbon-13 delta shifts and steric interactions in N-Aryl-1-isoindolinones and -isoindoline-1,3-diones was written by Khadim, Mohammad A.;Colebrook, L. D.. And the article was included in Magnetic Resonance in Chemistry in 1985.Quality Control of 2-Phenylisoindolin-1-one This article mentions the following:

Consistently deshielding ¹³C 闂?shifts resulting from the presence of aryl ortho substituents are determined for the 3-methylene C atoms of N-aryl-1-isoindolinones (0.12-3.25 ppm) and for the C:O group C atoms of these compounds and corresponding N-arylisoindoline-1,3-diones (0.04-1.47 ppm). Low-temperature (-75 and -150 闂? ¹H NMR studies indicate that steric barriers to internal rotation about the aryl C-N bonds in the N-aryl-1-isoindolinones are low. The compounds with the bulkiest aryl ortho substituents tend to show the largest 闂?shifts (particularly for the 3-methylene C atoms). No consistent correlation with the size of aryl ortho-substituents or their expected electronic properties is evident. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Quality Control of 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 2-Phenylisoindolin-1-one

Referemce:
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

Metabolomics-assisted discovery of a new anticancer GLS-1 inhibitor chemotype from a nortopsentin-inspired library: From phenotype screening to target identification was written by Carbone, Daniela;Vestuto, Vincenzo;Ferraro, Maria Rosalia;Ciaglia, Tania;Pecoraro, Camilla;Sommella, Eduardo;Cascioferro, Stella;Salviati, Emanuela;Novi, Sara;Tecce, Mario Felice;Amodio, Giuseppina;Iraci, Nunzio;Cirrincione, Girolamo;Campiglia, Pietro;Diana, Patrizia;Bertamino, Alessia;Parrino, Barbara;Ostacolo, Carmine. And the article was included in European Journal of Medicinal Chemistry in 2022.Product Details of 90271-86-6 This article mentions the following:

The enzyme glutaminase-1 (GLS-1) has shown a clear and coherent implication in the progression and exacerbation of different aggressive tumors such as glioblastoma, hepatocarcinoma, pancreas, bone, and triple-neg. breast cancer. Few chemotypes are currently available as selective GLS-1 inhibitors, and still, fewer of them are at the clin. stage. In the present paper, starting from a naturally-inspired antitumor compound library, metabolomics has been used to putatively identify the mol. mechanism underlying biol. activity. GLS-1 was identified as a potential target. Biochem. anal. confirmed the hypothesis leading to the identification of a new hit compound acting as a GLS-1 selective inhibitor (IC₅₀ = 3.96 闂?1.05 濠电偞鎸鹃幏?, compared to the GLS-2 isoform (IC₅₀ = 12.90 闂?0.87 濠电偞鎸鹃幏?, with remarkable antitumor potency over different aggressive tumor cell lines. Mol. modeling studies revealed new insight into the drug-target interaction providing robust SAR clues for the rational hit-to-lead development. The approach undertaken underlines the wide potential of metabolomics applied to drug discovery, particularly in target identification and hit discovery following phenotype screening. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Product Details of 90271-86-6).

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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.Product Details of 90271-86-6

Referemce:
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

Preparation of Functionalized Arylmagnesium Reagents Bearing an o-Chloromethyl Group was written by Delacroix, Thomas;Berillon, Laurent;Cahiez, Gerard;Knochel, Paul. And the article was included in Journal of Organic Chemistry in 2000.Formula: C14H11NO This article mentions the following:

The selective iodine-magnesium exchange of 2-chloromethyl-1-iodobenzenes such as 3,2-I(ClCH₂)C₆H₃R (R = H CO₂Me) are reported. The resulting organomagnesium reagents 3,2-(BrMg)(ClCH₂)C₆H₃R (R = same as above) are synthetic equivalent of a zwitterionic synthon and prove to be well suited for participation in cyclization reactions. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Formula: C14H11NO).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C14H11NO

Referemce:
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

New Generation of Selective Androgen Receptor Degraders: Our Initial Design, Synthesis, and Biological Evaluation of New Compounds with Enzalutamide-Resistant Prostate Cancer Activity was written by Hwang, Dong-Jin;He, Yali;Ponnusamy, Suriyan;Mohler, Michael L.;Thiyagarajan, Thirumagal;McEwan, Iain J.;Narayanan, Ramesh;Miller, Duane D.. And the article was included in Journal of Medicinal Chemistry in 2019.Electric Literature of C8H6N2O2 This article mentions the following:

In our effort to find small-mol. treatments of advanced prostate cancers (PCs), a novel series of indolyl and indolinyl propanamides (series II and III) were discovered as selective androgen receptor degraders (SARDs). Initial studies of androgen receptor (AR) antagonist (1) and agonist (2) propanamides yielded a tertiary aniline (3) with novel SARD activity but poor metabolic stability. Cyclization to II and III produced submicromolar AR antagonism and protein degradation selective to AR and AR splice variant (AR SV). II and III maintained potency against enzalutamide-resistant (Enz-R) mutant ARs and PC cells and were efficacious in Enz-R xenografts, suggesting their potential to treat advanced PCs. Design, synthesis, and biol. activity of novel SARDs that could potentially be used for the treatment of a wide spectrum of PCs including castration-resistant, Enz-R, and/or AR SV-dependent advanced PCs that are often untreatable with known hormone therapies are discussed. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C8H6N2O2

Referemce:
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

Synthesis of 3-indoleacetic acids and 2-carboxy-3-indoleacetic acids with substituents in the benzene ring was written by Fox, Sidney W.;Bullock, Milon W.. And the article was included in Journal of the American Chemical Society in 1951.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Preceding abstract Cyclization of the corresponding succinaldehydic acid phenylhydrazones yielded the following 3-indoleacetic acid derivatives (m.p. and yield (%) given): 5-Cl, 158-9.5闂?(decomposition), 20; 7-Cl, 164-5闂? 13; 5,7-di-Cl 194-7闂?(decomposition), 9; 5-Me, 151-2闂? 31; 4-Cl, 185-7闂?(decomposition), 19; 6-Cl, 187-8闂?(decomposition), 26; 4- and 6-Cl eutectic mixture, 158-9闂?(decomposition), 16. 2,6-Cl(O₂N)C₆H₄Me (Uhle, C.A. 43, 4255d) yielded 4-chloroindole (I), b₁₃ 150闂? n_D²⁰ 1.6286, d₂₀²⁰ 1.259. I (8.0 g.), 4.3 g. 36% HCHO, 9.3 g. 25% Me₂NH, and 26 cc. AcOH allowed to stand at room temperature overnight, distilled in vacuo, 75 cc. water added, and the mixture filtered and made alk. with N NaOH yielded 8.4 g. 4-chlorogramine (II), m. 147-8.5闂?(150-1闂?when heated fairly rapidly) (from Me₂CO). Attempted conversion of II to 4-chloro-3-indoleacetic acid yielded a small amount of crude acid and an unidentified, higher-melting solid. 4,2-Cl-(O₂N)C₆H₃Me yielded 6-chloro-2-indolecarboxylic acid (III), m. 242-4闂?(decomposition) (from aqueous EtOH). III (8.8 g.) added to 60 cc. tech., anhydrous quinoline containing 5 g. CuCl at 150闂? the mixture heated 3 h. at 240闂?(bath temperature), cooled, triturated with Et₂O, shaken with water, the solid filtered off, washed with dilute HCl and Et₂O, the water-Et₂O mixture acidified with HCl, and the Et₂O distilled yielded 5 g. 6-chloroindole (IV), m. 83.6闂? EtMgI (35 cc. of a 0.033 M solution) added to 5 g. IV in 25 cc. Et₂O, the mixture stirred at ice-bath temperature 1 h., 2.8 g. ClCH₂CN in 25 cc. Et₂O added dropwise, the mixture stirred 30 min. at 0闂? refluxed 4 h., cooled, 3 cc. AcOH in 50 cc. water added, then 50 cc. C₆H₆, the mixture allowed to stand overnight, the aqueous layer extracted with C₆H₆ (solid discarded), the Et₂O-C₆H₆ layer distilled, the residue distilled at 160-80闂?0.2, the distillate refluxed 4 h. with 10 cc. MeOH and 20 cc. 20% aqueous KOH, filtered with C through diatomaceous earth, the filtrate extracted with Et₂O, and the aqueous layer acidified yielded 1.8 g. 6-chloro-3-indoleacetic acid. Cyclization of the 婵?ketoglutaric acid phenylhydrazones obtained as byproducts yielded the following 2-carboxy-3-indoleacetic acids (m.p. (decomposition), and yield (%) given): 7-Cl, 253闂? 31; 5-Me, 243闂? -; 7-Me, 228-9闂? 6; 5-Br, 247-8闂? 13. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid

Referemce:
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

Synthesis of Quinoline-4-carboxamides and Quinoline-4-carboxylates via a Modified Pfitzinger Reaction of N-Vinylisatins was written by Mijangos, Marco V.;Amador-Sanchez, Yoarhy A.;Miranda, Luis D.. And the article was included in European Journal of Organic Chemistry in 2021.Recommanded Product: 150560-58-0 This article mentions the following:

A synthetic approach for the accelerated assembly of quinoline-4-carboxamide and quinoline-4-carboxylate nuclei is presented. The methodol. is based on the rearrangement of N-vinylisatins promoted by different types of amines (or ethanol) in a Pfitzinger-type mechanism that, in turn, builds the quinoline ring system. The reaction took place only by heating the starting materials in ethanol, without any additive. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Recommanded Product: 150560-58-0).

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

Referemce:
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