indole-building-block | - Page 82 of 1434

Muvvala, Subhashini et al. published their research in ChemistrySelect 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. 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.Name: 2-Phenylisoindolin-1-one

Microwave-Assisted Reductive Amination of 2-Carboxybenzaldehydes with Amines for the Synthesis of N-Substituted Isoindolin-1-ones was written by Muvvala, Subhashini;Kumari, Krishnaiah;Miriyala, Venkatesh;Mogili, Padma;Chidara, Sridhar;Maddirala, Shambabu Joseph;Saxena, Abhishek;Behera, Manoranjan. And the article was included in ChemistrySelect in 2022.Name: 2-Phenylisoindolin-1-one This article mentions the following:

Microwave-assisted, transition metal free methodol. for the synthesis of N-substituted isoindolin-1-ones I [R¹ = H, F; R² = i-Pr, Ph, PhCH₂, 2-(piperidin-1-yl)ethyl, etc.] from 2-carboxybenzaldehydes II and various amines R²NH₂ by reductive amination reaction using formic acid has been described. This method is relatively simple, benign, safe and tolerates a variety of functional groups. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 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

Porobic, Ivana et al. published their research in Bioorganic & Medicinal Chemistry in 2013 | 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid

Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid: A QSPR study was written by Porobic, Ivana;Kontrec, Darko;Soskic, Milan. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Three molecularly imprinted polymers (MIPs) were prepared using the phytohormone indole-3-acetic acid (IAA) as a template mol., 4-vinylpyridine (MIP-1 and MIP-2) or N,N-dimethylaminoethyl methacrylate (MIP-3) as functional monomers, ethylenglycol dimethacrylate as a cross linker and acetonitrile (MIP-1), a methanol-water mixture (MIP-2) or chloroform (MIP-3) as porogens. Retention factors for IAA and 29 indole derivatives were determined by high-performance liquid chromatog., using the molecularly imprinted polymers as stationary phases and acetonitrile as an eluent. High correlations between selectivity factors of above mentioned polymers indicate that their retention mechanisms are basically the same. A quant. structure-property relationships anal. revealed that the presence of the terminal carboxyl group on the 3-side chain plays an essential role in the binding of the indole derivatives to the polymers. The derivatives without the carboxyl group exhibit a drastically lower affinity toward the polymers. Another factor which favors the binding is electronic d. of indole nucleus. Substituents with electro-withdrawing properties enhance the binding, while electro-donating substituents have the opposite effect. The length of the 3-side chain also affects the binding. Indole-3-carboxylic acid having the carboxyl group directly attached to the ring as well as the derivatives whose side chain is longer than that of IAA bind to the polymers with a lower affinity. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid).

Zhang, Shunji et al. published their research in Youji Huaxue in 2020 | 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). Recommanded Product: 6-Nitro-1H-indole

Sulfuric acid catalyzed rapid nucleophilic substitution of propargyl alcohols was written by Zhang, Shunji;Liu, Huili. And the article was included in Youji Huaxue in 2020.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

Sulfuric acid efficiently catalyzes the direct substitution of the hydroxyl group of propargylic alcs. R¹C(OH)CCR² (R¹ = 3,4-dimethoxyphenyl, 4-(benzyloxy)phenyl, 3-(trifluoromethyl)phenyl, etc.; R² = pentyl, Ph, 4-methoxyphenyl) with a variety of C- and O-based nucleophiles such as isopropanol, phenol, furan, etc. to aid C-C and C-O bond formation. The reactions can be performed in an undried solvent under air atm. to obtain the desired products R¹C(R³)CCR² (R³ = OMe, furan-2-yl, 4-hydroxyphenyl, etc.) in good yields. In most cases, the reaction proceeds to completion in 1 min at room temperature In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).

Baykal, Aslihan et al. published their research in European Journal of Organic Chemistry in 2020 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 210345-56-5

A Bu₄N[Fe(CO)₃(NO)]-Catalyzed Hemetsberger-Knittel Indole Synthesis was written by Baykal, Aslihan;Plietker, Bernd. And the article was included in European Journal of Organic Chemistry in 2020.Recommanded Product: 210345-56-5 This article mentions the following:

The nucleophilic Fe complex Bu₄N[Fe(CO)₃(NO)] (TBA[Fe]) catalyzes the direct intramol. amination of aryl vinyl azides RCH=C(N₃)C(O)R¹ (R = 3,4-dimethoxyphenyl, 4,5-dimethylfuran-2-yl, naphthalen-1-yl, etc.; R¹ = Ph, OMe, morpholin-4-yl, etc.) to give the corresponding indole derivatives I (R² = H, F, CN, dimethylaminyl, etc.; R³ = H, Br, OMe; R⁴ = H, Br, Me, OMe; R³R⁴ = -(CH=CH-CH=CH)-; R⁵ = H, Me), Me 2,3-dimethyl-4H-furo[3,2-b]pyrrole-5-carboxylate and Me pyrazolo[1,5-a]pyridine-2-carboxylate in good to excellent yields. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: 210345-56-5).

Lai, Mei-Jung et al. published their research in European Journal of Medicinal Chemistry in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.COA of Formula: C8H6N2O2

1-Arylsulfonyl indoline-benzamides as a new antitubulin agents, with inhibition of histone deacetylase was written by Lai, Mei-Jung;Ojha, Ritu;Lin, Mei-Hsiang;Liu, Yi-Min;Lee, Hsueh-Yun;Lin, Tony Eight;Hsu, Kai-Cheng;Chang, Chi-Yen;Chen, Mei-Chuan;Nepali, Kunal;Chang, Jang-Yang;Liou, Jing-Ping. And the article was included in European Journal of Medicinal Chemistry in 2019.COA of Formula: C8H6N2O2 This article mentions the following:

We report structure-activity relationships of 1-arylsulfonyl indoline based benzamides. The benzamide (9) exhibits striking tubulin inhibition with an IC₅₀ value of 1.1 濠电偞鎸鹃幏? better than that of combretastain A-4 (3), and substantial antiproliferative activity against a variety of cancer cells, including MDR-pos. cell lines with an IC₅₀ value of 49 nM (KB), 79 nM (A549), 63 nM (MKN45), 64 nM (KB-VIN10), 43 nM (KB-S15), and 46 nM (KB-7D). Dual inhibitory potential of compound 9 was found as it demonstrated significant inhibitory potential against HDAC1, 2 and 6 in comparison to MS-275 (6). Some key interactions of 9 with the amino acid residues of the active site of tubulin and with amino acid residues of HDAC 1 isoform have been figured out by mol. modeling. Compound 9 also demonstrated significant in vivo efficacy in the human non-small cell lung cancer A549 xenograft model as well as B-cell lymphoma BJAB xenograft tumor model. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4COA of Formula: C8H6N2O2).

Hegedus, Louis S. et al. published their research in Journal of Organic Chemistry in 1981 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Product Details of 6639-06-1

Palladium-assisted N-alkylation of indoles: attempted application to polycyclization was written by Hegedus, Louis S.;Winton, Peter M.;Varaprath, Sudarsanan. And the article was included in Journal of Organic Chemistry in 1981.Product Details of 6639-06-1 This article mentions the following:

The palladium(II) complexes of the olefins ethene, propene, and 1-hexene reacted with 1-lithioindole to produce N-alkylated indoles exclusively. Attempts to perform this N-alkylation intramol. (to form tricyclic material from 2-allylskatole) failed. Anilines with dienic side chains in the 2-position were subjected to Pd(II)-assisted cyclization conditions in attempts to induce polycyclization. However, only monocyclization was observed In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Product Details of 6639-06-1).

Islam, Mohammad Shahidul et al. published their research in ACS Omega in 2021 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 827-01-0

Construction of Spirooxindole Analogues Engrafted with Indole and Pyrazole Scaffolds as Acetylcholinesterase Inhibitors was written by Islam, Mohammad Shahidul;Al-Majid, Abdullah Mohammed;Azam, Mohammad;Verma, Ved Prakash;Barakat, Assem;Haukka, Matti;Elgazar, Abdullah A.;Mira, Amira;Badria, Farid A.. And the article was included in ACS Omega in 2021.Recommanded Product: 827-01-0 This article mentions the following:

Twenty-five new hits of spirooxindole analogs engrafted with indole and pyrazole scaffolds were designed and constructed via a [3+2]cycloaddition (32CA) reaction starting from three components: new chalcone-based indole and pyrazole scaffolds, substituted isatins, and secondary amines. The potency of the compounds were assessed in modulating cholinesterase (AChE) activity using Ellman’s method. Two compounds showed the strongest acetylcholine esterase inhibition (AChEI) with IC₅₀ values of 24.1 and 27.8濠电偞鎸鹃幏? resp. Mol. docking was used to study their interaction with the active site of hAChE. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 827-01-0).

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).

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).

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).