22/11/2022 - Page 2 of 6 - Indole Building Blocks

Ogurtsov, Vladimir A. et al. published their research in Molbank in 2021 | CAS: 1242338-94-8

Indolin-5-ylmethanamine dihydrochloride (cas: 1242338-94-8) 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.Electric Literature of C9H14Cl2N2

(2,3-Dihydro-1H-indol-5-ylmethyl)amine was written by Ogurtsov, Vladimir A.;Rakitin, Oleg A.. And the article was included in Molbank in 2021.Electric Literature of C9H14Cl2N2 The following contents are mentioned in the article:

New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental anal., high resolution mass-spectrometry, ¹H, ¹³C NMR and IR spectroscopy and mass-spectrometry. The resulting compound is a convenient intermediate for various disubstituted 1-(indolin-5-yl)methanamines, which may be of interest as substances with useful pharmacol. properties. This study involved multiple reactions and reactants, such as Indolin-5-ylmethanamine dihydrochloride (cas: 1242338-94-8Electric Literature of C9H14Cl2N2).

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

Zhang, Xiyuan et al. published their research in Organic Letters in 2022 | CAS: 100831-25-2

7-Bromo-1-methylindolin-2-one (cas: 100831-25-2) 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: 100831-25-2

Ligand-Controlled Palladium-Catalyzed Asymmetric [4+3] and [2+3] Annulation Reactions of Spirovinylcyclopropyl Oxindoles with o-Quinone Methides was written by Zhang, Xiyuan;Zhang, Cong;Jiang, Bo;Gao, Yanfeng;Xu, Xiufang;Miao, Zhiwei. And the article was included in Organic Letters in 2022.HPLC of Formula: 100831-25-2 The following contents are mentioned in the article:

Herein, the regiodivergent ligand-controlled palladium-catalyzed asym. cycloaddition reactions between spirovinylcyclopropyl oxindoles and o-quinone methides was reported. Specifically, by using the chiral P,P-ligand Segphos, various spirooxindole-3,4-benzo[b]oxepanes in moderate to good yields with excellent enantioselectivities via [4+3] cycloaddition reactions was obtained. In contrast, reactions involving Trost’s ligand showed different regio- and stereoselectivities, affording bispirooxindole heterocyclic compounds in good yields via [2+3] cycloaddition reactions. This study involved multiple reactions and reactants, such as 7-Bromo-1-methylindolin-2-one (cas: 100831-25-2HPLC of Formula: 100831-25-2).

Rana, Sandeep et al. published their research in Journal of Medicinal Chemistry in 2016 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C10H9NO2

Isatin Derived Spirocyclic Analogues with α-Methylene-γ-butyrolactone as Anticancer Agents: A Structure-Activity Relationship Study was written by Rana, Sandeep;Blowers, Elizabeth C.;Tebbe, Calvin;Contreras, Jacob I.;Radhakrishnan, Prakash;Kizhake, Smitha;Zhou, Tian;Rajule, Rajkumar N.;Arnst, Jamie L.;Munkarah, Adnan R.;Rattan, Ramandeep;Natarajan, Amarnath. And the article was included in Journal of Medicinal Chemistry in 2016.Electric Literature of C10H9NO2 The following contents are mentioned in the article:

Design, synthesis, and evaluation of α-methylene-γ-butyrolactone analogs and their evaluation as anticancer agents is described. SAR identified a spirocyclic analog I that inhibited TNFα-induced NF-κB activity, cancer cell growth and tumor growth in an ovarian cancer model. A second iteration of synthesis and screening identified II which inhibited cancer cell growth with low-μM potency. Our data suggest that an isatin-derived spirocyclic α-methylene-γ-butyrolactone is a suitable core for optimization to identify novel anticancer agents. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Electric Literature of C10H9NO2).

Wang, Minghua et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2015 | CAS: 1190314-60-3

5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 1190314-60-3

Synthesis and antitumor activity of 5-(5-halogenated-2-oxo-1H-pyrrolo[2,3-b]pyridin-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamides was written by Wang, Minghua;Ye, Cheng;Liu, Mingliang;Wu, Zhaoyang;Li, Linhu;Wang, Chunlan;Liu, Xiujun;Guo, Huiyuan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Product Details of 1190314-60-3 The following contents are mentioned in the article:

We report herein the design and synthesis of a series of novel 5-halogenated-7-azaindolin-2-one derivatives containing a 2,4-dimethylpyrrole moiety. Nine target compounds with ≥70% inhibition against MCF-7 at 30 μM were further evaluated for their in vitro antitumor activity against seven human cancer cell lines by SRB assay. Results reveal that some compounds have potent antitumor activity, and the most active I (IC₅₀s: 4.49-15.39 μM) was found to be more active than Sunitinib (IC₅₀s: 4.70->30 μM) against all of the tested cancer cell lines. This study involved multiple reactions and reactants, such as 5-Chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (cas: 1190314-60-3Product Details of 1190314-60-3).

El-Sharief, A. M. S. et al. published their research in Indian Journal of Chemistry in 1981 | CAS: 82104-06-1

2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1) 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.Product Details of 82104-06-1

Monothio- and dithiophthalimides: synthesis of dibromo-β-isoindigo and dibromodithio-β-isoindigo derivatives was written by El-Sharief, A. M. S.;Hammad, N. E.. And the article was included in Indian Journal of Chemistry in 1981.Product Details of 82104-06-1 The following contents are mentioned in the article:

5-Bromo-3-oxo-1-thioxoisoindolines and 5-bromo-1,3-dithioxoisoindolines on reaction with amines either in AcOH or under fusion give 2-aryl-1-arylimino-5-bromo-3-isoindolinones and 1-arylimino-5-bromo-3-thioxoisoindolines, resp. Dithione I on reaction with Ph₂CN₂ gives the spiro[isoindoline-thiirane] II. The 5-bromo-3-oxo-1-thioxoisoindolines and 5-bromo-1,3-dithioxoisoindolines when heated with Cu turnings in decalin give the corresponding dibromo-β-isoindigo derivatives e.g. III and dibromodithio-β-isoindigo derivs, e.g. IV. This study involved multiple reactions and reactants, such as 2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1Product Details of 82104-06-1).

Drung, Binia et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2014 | CAS: 146436-31-9

1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (cas: 146436-31-9) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application of 146436-31-9

Computational & experimental evaluation of the structure/activity relationship of β-carbolines as DYRK1A inhibitors was written by Drung, Binia;Scholz, Christoph;Barbosa, Valeria A.;Nazari, Azadeh;Sarragiotto, Maria H.;Schmidt, Boris. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2014.Application of 146436-31-9 The following contents are mentioned in the article:

DYRK1A has been associated with Down’s syndrome and neurodegenerative diseases, therefore it is an important target for novel pharmacol. interventions. We combined a ligand-based pharmacophore design with a structure-based protein/ligand docking using the software MOE in order to evaluate the underlying structure/activity relationship. Based on this knowledge we synthesized several novel β-carboline derivatives to validate the theor. model. Furthermore we identified a modified lead structure as a potent DYRK1A inhibitor (IC₅₀ = 130 nM) with significant selectivity against MAO-A, DYRK2, DYRK3, DYRK4 & CLK2. This study involved multiple reactions and reactants, such as 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (cas: 146436-31-9Application of 146436-31-9).

Zhang, Nanjing et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2016 | CAS: 1000343-16-7

5-Fluoro-6-methyl-1H-indole (cas: 1000343-16-7) 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.Recommanded Product: 5-Fluoro-6-methyl-1H-indole

Discovery of 2-(4-sulfonamidophenyl)-indole 3-carboxamides as potent and selective inhibitors with broad hepatitis C virus genotype activity targeting HCV NS4B was written by Zhang, Nanjing;Turpoff, Anthony;Zhang, Xiaoyan;Huang, Song;Liu, Yalei;Almstead, Neil;Njoroge, F. George;Gu, Zhengxian;Graci, Jason;Jung, Stephen P.;Pichardo, John;Colacino, Joseph;Lahser, Fred;Ingravallo, Paul;Weetall, Marla;Nomeir, Amin;Karp, Gary M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Recommanded Product: 5-Fluoro-6-methyl-1H-indole The following contents are mentioned in the article:

A novel series of 2-(4-sulfonamidophenyl)-indole 3-carboxamides was identified and optimized for activity against the HCV genotype 1b replicon resulting in compounds with potent and selective activity. Further evaluation of this series demonstrated potent activity across HCV genotypes 1a, 2a and 3a. Compound I had reduced activity against HCV genotype 1b replicons containing single mutations in the NS4B coding sequence (F98C and V105M) indicating that NS4B is the target. This novel series of 2-(4-sulfonamidophenyl)-indole 3-carboxamides serves as a promising starting point for a pan-genotype HCV discovery program. This study involved multiple reactions and reactants, such as 5-Fluoro-6-methyl-1H-indole (cas: 1000343-16-7Recommanded Product: 5-Fluoro-6-methyl-1H-indole).

Martinez-Gudino, Gelacio et al. published their research in Journal of Molecular Structure in 2019 | CAS: 885272-25-3

2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid (cas: 885272-25-3) 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). Application In Synthesis of 2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid

Mechanistic study of reversible solid-state melt isomerization of 2-oxindoles to 2-quinolinones and its occurrence in a mass spectrometer was written by Martinez-Gudino, Gelacio;Perez-Rojas, Nadia A.;Trujillo-Serrato, Joel J.;Mora-Perez, Yolanda;Suarez-Castillo, Oscar R.;Morales-Rios, Martha S.. And the article was included in Journal of Molecular Structure in 2019.Application In Synthesis of 2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid The following contents are mentioned in the article:

An eco-friendly equilibrated rearrangement of a series of 2-oxo-3-indolyl acetic acids (1) with 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid derivatives (2) was investigated through a solid state melt reaction (SSMR). Mechanistic insight into the thermal rearrangement is provided by ¹³C-isotopic labeling. The standard mass spectra of 1 and 2 were virtually identical preventing their reliable identification. Reversible interconversion of 1 and 2 was evidenced to occur in the inlet system of a mass spectrometer under electron impact conditions. Relative abundances of fragment ions were found to be a function of temperature This study involved multiple reactions and reactants, such as 2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid (cas: 885272-25-3Application In Synthesis of 2-(5-Methoxy-2-oxoindolin-3-yl)acetic acid).

Baxter, Gary J. et al. published their research in Australian Journal of Chemistry in 1975 | CAS: 15540-90-6

4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Reference of 15540-90-6

Methyleneketenes and methylenecarbenes. V. Condensation of ketones with isopropylidene malonate catalyzed by titanium tetrachloride and synthesis of a dibenzofuran was written by Baxter, Gary J.;Brown, Roger F. C.. And the article was included in Australian Journal of Chemistry in 1975.Reference of 15540-90-6 The following contents are mentioned in the article:

The TiCl4-pyridine-THF reagent of Lehnert will effect direct condensation of some aromatic ketones RCOR1(R = Ph, o-tolyl, 2,5-dimethyl-3-furyl; R1 = Me, Ph, Co2Me, piperidinocarbonyl; RR1 = 2,2′-biphenylylene) with isopropylidene malonate (Meldrum’s acid) to give I. The synthetic value of this reaction is explored in a synthesis of 7-methoxy-9-methyldibenzofuran-3-ol involving pyrolysis of I (R = 2,5-dimethyl-3-furyl), formylation of II with Cl2CHOMe and SnCl4, conversion of III to the 6-MeO analog. condensation with isopropylidene malonate, and pyrolysis of the product. A 1,9-dimethyldibenzofuran related to strepsilin could not be obtained in the same way. This study involved multiple reactions and reactants, such as 4,7-Dimethylindoline-2,3-dione (cas: 15540-90-6Reference of 15540-90-6).

Herraiz, Tomas et al. published their research in American Journal of Enology and Viticulture in 1994 | CAS: 146436-31-9

1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (cas: 146436-31-9) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Quality Control of 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

Separation and characterization of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acids by HPLC and GC-MS. Identification in wine samples was written by Herraiz, Tomas;Ough, C. S.. And the article was included in American Journal of Enology and Viticulture in 1994.Quality Control of 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid The following contents are mentioned in the article:

1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acids, products of the reaction of tryptophan and aldehydes in alc. fermented beverages, were isolated by solid phase extraction, analyzed by HPLC, and identified by gas chromatog. and mass spectrometry after derivatization to form N-trifluoroacetyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid Me esters. 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid (THCA) and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (both diastereoisomers) were pos. identified in wine samples. 1-Ethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (ETCA) and 1-isobutyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (IBTCA) were not identified in the wines studied. This study involved multiple reactions and reactants, such as 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (cas: 146436-31-9Quality Control of 1-Isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid).