20/02/2023 - Page 10 of 14 - Indole Building Blocks

Kryshchyshyn-Dylevych, Anna et al. published their research in Synthetic Communications in 2020 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 167631-84-7

Synthesis and anticancer activity evaluation of 3-(4-oxo-2-thioxothiazolidin-5-yl)-1H-indole-carboxylic acids derivatives was written by Kryshchyshyn-Dylevych, Anna;Garazd, Myroslav;Karkhut, Andrew;Polovkovych, Sviatoslav;Lesyk, Roman. And the article was included in Synthetic Communications in 2020.Recommanded Product: 167631-84-7 This article mentions the following:

A mild and efficient method for the synthesis of 1-oxo-9H-thiopyrano[3,4-b]indole-3-carboxylic acids I (R = F, H, OMe) and dimerized 3-(4-carboxy-1H-3-indolyl)-2-propenoic acids II (R¹ = Me, Et) via alk. hydrolysis of 3-(rhodanin-5-yl)-1H-indole-2-carboxylic acids derivatives III (R² = H, methoxycarbonyl; R³ = H, methoxycarbonyl, carboxy; R⁴ = H, Me, Et) was elaborated. Anticancer activity screening in NCI60-cell lines assay allowed identification of III (R = F; R² = R⁴ = H; R³ = methoxycarbonyl) with significant antimitotic activity at micromolar and submicromolar concentrations In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Recommanded Product: 167631-84-7).

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

Abu Khalaf, Reema et al. published their research in Molecular Diversity in 2022 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application In Synthesis of Methyl 5-fluoro-1H-indole-2-carboxylate

Discovery, synthesis and in combo studies of Schiff闂備胶鍋ㄩ崕鎶芥倶?bases as promising dipeptidyl peptidase-IV inhibitors was written by Abu Khalaf, Reema;Awad, Maha;Al-Essa, Luay;Mefleh, Sara;Sabbah, Dima;Al-Shalabi, Eveen;Shabeeb, Ihsan. And the article was included in Molecular Diversity in 2022.Application In Synthesis of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

Diabetes mellitus is a main global health apprehension. Macrovascular illnesses, neuropathy, retinopathy, and nephropathy are considered some of its severe hitches. Gliptins are a group of hypoglycemic agents that inhibit dipeptidyl peptidase-IV (DPP-IV) enzyme and support blood glucose-lowering effect of incretins. In the current research, synthesis, characterization, docking, and biol. evaluation of fourteen Schiff闂備胶鍋ㄩ崕鎶芥倶?bases 5a-f and 9a-h were carried out. Compound 9f revealed the best in vitro anti-DPP-IV activity of 35.7% inhibition at a concentration of 100 濠电偞鎸鹃幏? Compounds 9c and 9f with the highest in vitro DPP-IV inhibition were subjected to the in vivo glucose-lowering test using vildagliptin as a pos. inhibitor. Vildagliptin, 9c, and 9f showed significant reduction in the blood glucose levels of the treated mice after 30 min of glucose administration. Moreover, induced fit docking showed that these derivatives accommodated the enzyme binding site with comparable docking scores. Schiff闂備胶鍋ㄩ崕鎶芥倶?bases can serve as promising lead for the development of new DPP-IV inhibitors. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Application In Synthesis of Methyl 5-fluoro-1H-indole-2-carboxylate).

Apsel, Beth et al. published their research in Nature Chemical Biology in 2008 | 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.SDS of cas: 754214-56-7

Targeted polypharmacology: discovery of dual inhibitors of tyrosine and phosphoinositide kinases was written by Apsel, Beth;Blair, Jimmy A.;Gonzalez, Beatriz;Nazif, Tamim M.;Feldman, Morri E.;Aizenstein, Brian;Hoffman, Randy;Williams, Roger L.;Shokat, Kevan M.;Knight, Zachary A.. And the article was included in Nature Chemical Biology in 2008.SDS of cas: 754214-56-7 This article mentions the following:

The clin. success of multitargeted kinase inhibitors has stimulated efforts to identify promiscuous drugs with optimal selectivity profiles. It remains unclear to what extent such drugs can be rationally designed, particularly for combinations of targets that are structurally divergent. Here we report the systematic discovery of mols. that potently inhibit both tyrosine kinases and phosphatidylinositol-3-OH kinases, two protein families that are among the most intensely pursued cancer drug targets. Through iterative chem. synthesis, X-ray crystallog. and kinome-level biochem. profiling, we identified compounds that inhibit a spectrum of new target combinations in these two families. Crystal structures revealed that the dual selectivity of these mols. is controlled by a hydrophobic pocket conserved in both enzyme classes and accessible through a rotatable bond in the drug skeleton. We show that compound I blocks the proliferation of tumor cells by direct inhibition of oncogenic tyrosine kinases and phosphatidylinositol-3-OH kinases. These mols. demonstrate the feasibility of accessing a chem. space that intersects two families of oncogenes. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7SDS of cas: 754214-56-7).

Banjare, Shyam Kumar et al. published their research in Journal of Organic Chemistry in 2020 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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.Category: indole-building-block

Cobalt-Catalyzed One-Step Access to Pyroquilon and C-7 Alkenylation of Indoline with Activated Alkenes Using Weakly Coordinating Functional Groups was written by Banjare, Shyam Kumar;Biswal, Pragati;Ravikumar, Ponneri Chandrababu. And the article was included in Journal of Organic Chemistry in 2020.Category: indole-building-block This article mentions the following:

A new strategy for the C(7)-H functionalization of indoline derivatives using first-row transition-metal cobalt was demonstrated wherein the pivaloyl group acts as a weakly coordinating directing group. Biol. important pyroquilon(tetrahydropyroquinolinone) derivatives were synthesized in a one-pot manner through selective C(7)-H functionalization and concomitant cyclization. In this process, aromatic C-H and amidic C-N bonds were cleaved and new C-C and C-N bonds were formed in a step-economical fashion. Further, selective C(7)-H alkenylation of indoline derivatives was also accomplished using activated alkenes by varying the reaction conditions. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Category: indole-building-block).

Zhou, Feng et al. published their research in Zhongguo Yiyao Gongye Zazhi in 2013 | CAS: 320734-35-8

7-Bromooxindole (cas: 320734-35-8) 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. 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). Computed Properties of C8H6BrNO

Synthesis of substituted 1,3-dihydroindolin-2-ones was written by Zhou, Feng;Zheng, Canhui;Zhu, Ju;Liu, Jia;Zhou, Youjun. And the article was included in Zhongguo Yiyao Gongye Zazhi in 2013.Computed Properties of C8H6BrNO This article mentions the following:

The substituted 1,3-dihydroindolin-2-one compounds 1a-1k, the intermediates of tyrosine kinase inhibitors such as sunitinib, were synthesized from substituted anilines by acylation and cyclization to give substituted isatin derivatives followed by reduction with triethylsilane/trifluoroacetic acid. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8Computed Properties of C8H6BrNO).

Peters, A. T. et al. published their research in Journal of the Chemical Society in 1948 | 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.Name: 2-Phenylisoindolin-1-one

Reaction of certain diazosulfonates derived from 2-naphthol-1-sulfonic acid. XXVI. Phthalazine and isoindolinone compounds derived from aniline was written by Peters, A. T.;Rowe, F. M.;Brodrick, C. I.. And the article was included in Journal of the Chemical Society in 1948.Name: 2-Phenylisoindolin-1-one This article mentions the following:

PhN₂Cl (from 100 g. PhNH₂), added to an ice-cold solution of 400 g. 50% 2,1-HOC₁₀H₆SO₃Na in 1200 cc. H₂O, the 2-naphthol-1-benzenediazosulfonate (salted out with NaCl) converted by 100 g. Na₂CO₃ in 400 cc. H₂O at 0闂?to Na 1-benzeneazo-2-naphthoquinone-1-sulfonate (I), the mixture (after 15 min.) treated at 5闂?with 100 g. NaOH in 300 cc. H₂O, and then (after 15 min.) acidified with HCl at a temperature below 10闂? gives a tar which, on solution in NH₄OH and addition to boiling dilute HCl, gives 63% 1-hydroxy-3-phenyl-3,4-dihydro-4-phthalazineacetic acid (II), m. 264闂?(decomposition); Et ester, m. 91-2闂? boiling with Ac₂O 4 hrs. gives the O-acetate, m. 183闂? boiling with Ac₂O and a little C₅H₅N 50 hrs. gives also 4% of the internal anhydride of II, C₁₆H₁₂O₂N₂, m. above 320闂? 1-Keto-3-phenyl-2-methyltetrahydro-4-phthalazineacetic acid, m. 184-6闂? II (7 g.) and 15 cc. fuming HCl, heated 1 hr. at 180闂?and the product heated 10 min. with 15% Na₂CO₃, give 97% 3-phenyl-1-phthalazone (III), m. 208闂? turns green on standing (HCl salt, m. 162-4闂? picrate, yellow, m. 226闂?; Me₂SO₄ at 80闂?gives a resin which, boiled 5 min. with EtOH, gives the compound C₁₇H₁₈O₂N₂, m. 86-7闂? heated 4 hrs. at 140闂? this yields a compound C₁₆H₁₂ON₂, yellow, m. 234闂?(decomposition). III (2 g.), 140 cc. HCl, 80 cc. H₂O, 40 cc. EtOH, and 200 g. Zn-Hg, heated 4 hrs. at 70-80闂? give 85% 2-phenylphthalimidine. II (10 g.) in 70 cc. AcOH at 20闂? treated (2 hrs.) with 4 g. CrO₃ in 20 cc. AcOH and 10 cc. H₂O and the mixture kept overnight, gives 35.9% 3-phenyl-4-methyl-1-phthalazone (IV), m. 235闂?(picrate, yellow, m. 197闂?; 2 g. IV and 4 g. Na₂S₂O₄ in dilute aqueous NaOH, boiled 10 min., give 44.7% 1-keto-3-phenyl-4-methyltetrahydrophthalazine, m. 171闂? IV (3 g.), 70 cc. HCl, 50 cc. H₂O, and 90 g. Zn-Hg, boiled 4 hrs., give 2-phenyl-3-methylphthalimidine, m. 80闂? II (10 g.), added (30 min.) to 70 cc. HNO₃ at below 10闂?and the mixture poured onto ice, gives 73.6% of the 4′-NO₂ derivative of IV. II, refluxed 40 min. with aqueous H₂SO₄ (b. 140闂? or with equal volumes of H₂SO₄ and AcOH, gives 3-phenyl-1-phthalazone-x-sulfonic acid, prismatic needles with no m.p. I (from 50 g. PhNH₂) in aqueous Na₂CO₃ at 0闂? added to 50 g. NaOH in 180 cc. H₂O at 0闂? the mixture acidified after 5 min., the Na salt hydrolyzed, the acid solution evaporated to dryness, and the product extracted with and fractionated from AcOEt, gives 6.6 g. I; the more soluble fraction, boiled 5 min. with Ac₂O, gives 1.3 g. 2,5-diketo-3-phenylisoindolinopyrazolidocoline, m. 220-1闂? the 2,4-dinitrophenyl derivative m. 238-9闂?(cf. C.A. 42, 4568d). In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

Javid, Muhammad Tariq et al. published their research in Bioorganic Chemistry in 2018 | CAS: 150560-58-0

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

Synthesis, SAR elucidations and molecular docking study of newly designed isatin based oxadiazole analogs as potent inhibitors of thymidine phosphorylase was written by Javid, Muhammad Tariq;Rahim, Fazal;Taha, Muhammad;Nawaz, Mohsan;Wadood, Abdul;Ali, Muhammad;Mosaddik, Ashik;Shah, Syed Adnan Ali;Farooq, Rai Khalid. And the article was included in Bioorganic Chemistry in 2018.HPLC of Formula: 150560-58-0 This article mentions the following:

Thymidine phosphorylase is an enzyme involved in pyrimidine salvage pathway that is identical to platelet-derived endothelial cell growth factor (PD-ECGF) and gliostatin. It is enormously up regulated in a variety of solid tumors. Furthermore, surpassing of TP level protects tumor cells from apoptosis and helps cell survival. Thus TP is identified as a prime target for developing novel anticancer therapies. A new class of exceptionally potent isatin based oxadiazole (1-30) has been synthesized and evaluated for thymidine phosphorylase inhibitory potential. All analogs showed potent thymidine phosphorylase inhibition when compared with standard 7-Deazaxanthine, 7DX (IC₅₀=38.68闂?.12濠电偞鎸鹃幏?. Mol. docking study was performed in order to determine the binding interaction of these newly synthesized compounds, which revealed that these synthesized compounds established stronger hydrogen bonding network with active site of residues as compare to the standard compound 7DX. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0HPLC of Formula: 150560-58-0).

Kumar, Vishal et al. published their research in Green Chemistry in 2012 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 5388-42-1

Synthesis of substituted amines and isoindolinones: catalytic reductive amination using abundantly available AlCl₃/PMHS was written by Kumar, Vishal;Sharma, Sushila;Sharma, Upendra;Singh, Bikram;Kumar, Neeraj. And the article was included in Green Chemistry in 2012.Recommanded Product: 5388-42-1 This article mentions the following:

AlCl₃ has been employed for highly chemoselective reductive amination of carbonyl compounds in ethanol using polymethylhydrosiloxane as an inexpensive, stable and safe reducing agent without an inert atm. A large range of functional groups such as nitro, carboxylic acid, acetyl, nitrile, halogen, methoxy, alkene and heterocycles were well tolerated. AlCl₃ also catalyzed tandem amination-amidation of 2-carboxybenzaldehyde with different amines to afford N-substituted isoindolinones, e.g., I (R = H, Me, MeO, Ac, I, NO₂). The catalyst can be recycled at least three times without any significant effect on activity and selectivity. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 5388-42-1).

Pan, Yixiao et al. published their research in Advanced Synthesis & Catalysis in 2022 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 5388-42-1

Cobalt-Catalyzed Selective Transformation of Levulinic Acid and Amines into Pyrrolidines and Pyrrolidinones using Hydrogen was written by Pan, Yixiao;Luo, Zhenli;Yang, Ji;Han, Jiahong;Yang, Jianbo;Yao, Zhen;Xu, Lijin;Wang, Peng;Shi, Qian. And the article was included in Advanced Synthesis & Catalysis in 2022.Reference of 5388-42-1 This article mentions the following:

Cobalt-catalyzed selective transformation of levulinic acid and primary amines into pyrrolidines and pyrrolidinones under H₂ was developed. The catalyst system consisting of Co(NTf₂)₂, 1,1,1-tris(di(4-methoxyphenyl)phosphinomethyl) ethane ((p-anisyl)triphos) and Me₃SiOTf works well for the synthesis of pyrrolidines via reductive amination/cyclization/deoxygenative reduction of amide, and using Co(NTf₂)₂/1,1,1-tris(diphenylphosphinomethyl) ethane (triphos) as the catalyst under reduced hydrogen pressure results in exclusive formation of pyrrolidinones. Both aryl and alkyl primary amines are suitable substrates, and a variety of functional groups are tolerated. Meanwhile, 4-oxo-4-arylbutanoic acids, 5-oxohexanoic acid, 6-oxoheptanoic acid, 2-formylbenzoic acid, 2-acetylbenzoic acid and 2′-acetyl-[1,1′-biphenyl]-2-carboxylic acid are also applicable, allowing for convenient access to cyclic amines and lactams with different ring size. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

O’Sullivan, D. G. et al. published their research in Journal of the Chemical Society in 1957 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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

Influence of ortho substituents on the stretching frequencies of side-chain carbonyl groups in substituted benzenes was written by O’Sullivan, D. G.;Sadler, P. W.. And the article was included in Journal of the Chemical Society in 1957.Category: indole-building-block This article mentions the following:

Carbonyl frequencies for ortho-substituted benzoic acids, acetanilides, hydroxyimino acetanilides, anthranilic acids, and 4- and 7-substituted isatins are tabulated for NH₂, Me, H, F, I, Br, Cl, CF₃, and NO₂ as substituents. The frequencies increase with para-闂?(Hammett’s) values, with acidity of the correspondingly substituted pyridinium ions, with Taft’s 闂?sup>+-values (C.A. 46, 10793f; 48, 11287e) and are well correlated among each other. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Category: indole-building-block).