20/02/2023 - Indole Building Blocks

Qin, Mingze et al. published their research in Journal of Medicinal Chemistry in 2021 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester

Discovery of 4-Arylindolines Containing a Thiazole Moiety as Potential Antitumor Agents Inhibiting the Programmed Cell Death-1/Programmed Cell Death-Ligand 1 Interaction was written by Qin, Mingze;Meng, Yangyang;Yang, Haoshen;Liu, Lei;Zhang, Haotian;Wang, Simeng;Liu, Chunyang;Wu, Xia;Wu, Di;Tian, Ye;Hou, Yunlei;Zhao, Yanfang;Liu, Yajing;Xu, Congjun;Wang, Lihui. And the article was included in Journal of Medicinal Chemistry in 2021.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

Through specific structural modification of a 4-phenylindoline precursor, new 4-arylindolines containing a thiazole moiety were developed and found to be promising modulators of the programmed cell death-1 (PD-1)/programmed cell death-ligand 1 (PD-L1) axis. Compound A30(I) exhibited outstanding biochem. activity, with an IC₅₀ of 11.2 nM in a homogeneous time-resolved fluorescence assay. In the cell-based assay, A30 significantly promoted IFN-缂?secretion and rescued T-cell proliferation, which were inhibited by PD-1 activation. Furthermore, A30 showed favorable in vivo antitumor activity in a mouse 4T1 breast carcinoma model. Moreover, in mouse CT26 colon carcinoma models, A30 potently suppressed the growth of CT26/PD-L1 tumor but did not obviously affect the growth of CT26/vector tumor. The results of flow cytometry anal. indicated that A30 inhibited tumor growth by activating the immune microenvironment. We concluded that A30 is a new starting point for further development of PD-1/PD-L1 interaction inhibitors as antitumor agents. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

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

Do Minh, T. et al. published their research in Journal of Organic Chemistry in 1977 | 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 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). Reference of 5388-42-1

Reactions of phthalaldehyde with ammonia and amines was written by Do Minh, T.;Johnson, A. L.;Jones, J. E.;Senise, P. P. Jr.. And the article was included in Journal of Organic Chemistry in 1977.Reference of 5388-42-1 This article mentions the following:

Reactions of phthaladehyde with NH₃ and amines are described. Major products from NH₃ were phthalimidine and 3-(2-cyanophenyl)isoquinoline. Primary amines RNH₂ (R = Me, Ph, etc.) reacted with 2 moles of aldehyde to produce N-substituted adducts I, II whose steric requirements lead to unusual NMR spectra. At elevated temperatures unidentified colored materials were formed. 1-Hydroxyisoindoles are proposed intermediates. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Shershov, Valeriy E. et al. published their research in Dyes and Pigments in 2013 | CAS: 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C13H17NO3S

Near-infrared heptamethine cyanine dyes. Synthesis, spectroscopic characterization, thermal properties and photostability was written by Shershov, Valeriy E.;Spitsyn, Maksim A.;Kuznetsova, Viktoriya E.;Timofeev, Edward N.;Ivashkina, Olga A.;Abramov, Ivan S.;Nasedkina, Tatyana V.;Zasedatelev, Alexander S.;Chudinov, Alexander V.. And the article was included in Dyes and Pigments in 2013.Formula: C13H17NO3S This article mentions the following:

Near-IR heptamethine cyanine dyes were synthesized without substitution to the polyene chain but with various substituents on the indoleninium fragments. To develop indotricarbocyanine dyes with improved photochem. characteristics, we studied the relation between the structures of these compounds, their spectral properties, their photostability, and thermal stability. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Formula: C13H17NO3S).

Beckett, Arnold H. et al. published their research in Tetrahedron in 1968 | CAS: 20870-91-1

5-Amino-1-methyl-2-oxoindoline (cas: 20870-91-1) 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.Reference of 20870-91-1

Substituted oxindoles. I. The preparation and spectral characteristics of some simple oxindole derivatives was written by Beckett, Arnold H.;Daisley, R. W.;Walker, J.. And the article was included in Tetrahedron in 1968.Reference of 20870-91-1 This article mentions the following:

A series of oxindole derivatives substituted in the aromatic ring and their 1-Me homologs was prepared The effects of position and nature of substituents on the ir, N.M.R. and uv spectra were investigated. Evidence is presented which indicates the presence of an intermol. H bond in solutions of oxindole and certain 1-substituted derivatives A relation between the Hammett 闂?constant of substituents and the carbonyl frequencies of these oxindoles is reported. In the experiment, the researchers used many compounds, for example, 5-Amino-1-methyl-2-oxoindoline (cas: 20870-91-1Reference of 20870-91-1).

Cheng, Guangsheng et al. published their research in European Journal of Organic Chemistry in 2017 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C9H6ClNO

Isocyanide-Based Multicomponent Reaction To Furnish N-Functionalized Indoles by using N-Acyliminium Ions as Key Intermediates was written by Cheng, Guangsheng;Deng, Hongmei;He, Xiang;Gao, Yu;Li, Chunju;Jia, Xueshun;Li, Jian. And the article was included in European Journal of Organic Chemistry in 2017.Computed Properties of C9H6ClNO This article mentions the following:

The present work discloses an efficient multicomponent reaction of isocyanides, allenoates, and indoles. This protocol provides rapid and direct access to N-functionalized indoles from readily available starting materials, in the absence of any catalyst. The strategy also features a broad substrate scope and mild conditions. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).

Guarino, Victor R. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2020 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.COA of Formula: C14H9NO2S

An amide-based sulfenamide prodrug of gamma secretase inhibitor BMS-708163 delivers parent drug from an oral conventional solid dosage form in male beagle dog was written by Guarino, Victor R.;Olson, Richard E.;Everlof, J. Gerry;Wang, Nenghui;McDonald, Ivar;Haskell, Roy;Clarke, Wendy;Lentz, Kimberley A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.COA of Formula: C14H9NO2S This article mentions the following:

The objective of this Letter is to report the first (to our knowledge) in vivo proof of concept for a sulfenamide prodrug to orally deliver a poorly soluble drug containing a weakly-acidic NH-acid from a conventional solid dosage formulation. This proof of concept was established using BMS-708163 (1), a gamma secretase inhibitor containing a weakly acidic primary amide NH-acid as the chem. handle for attaching a series of thiol-based promoieties via a sulfenamide linkage. Aqueous stabilities and solubilities are reported for a series of six sulfenamide prodrugs (2-7) of 1. The sulfenamide prodrug containing the cysteine Me ester promoiety (5) was chosen for a orally-dosed PK study in male beagle dog comparing a solubilized formulation of 1 against a solid dosage form of 5 in a cross-over fashion at an equivalent molar dose of 3 mg/kg. Prodrug 5 delivered essentially a superimposable PK profile of 1 compared to the solubilized formulation of 1, without any detectable exposure of 5 in systemic circulation. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

Hopanna, Mamatha et al. published their research in Environmental Science & Technology in 2020 | 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. 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 C14H11NO

Photochemistry of the Organoselenium Compound Ebselen: Direct Photolysis and Reaction with Active Intermediates of Conventional Reactive Species Sensitizers and Quenchers was written by Hopanna, Mamatha;Kelly, Lisa;Blaney, Lee. And the article was included in Environmental Science & Technology in 2020.Electric Literature of C14H11NO This article mentions the following:

Ebselen (EBS), 2-phenyl-1,2-benzisoselenazol-3(2H)-one, is an organoselenium pharmaceutical with antioxidant and anti-inflammatory properties. Furthermore, EBS is an excellent scavenger of reactive oxygen species. This property complicates conventional protocols for sensitizing and quenching reactive species because of potential generation of active intermediates that quickly react with EBS. In this study, the photochem. reactivity of EBS was investigated in the presence of (1) ¹O₂ and ^{闂?/sup>OH sensitizers [rose Bengal (RB), perinaphthanone, and H₂O₂] and (2) reactive species scavenging and quenching agents (sorbic acid, isopropanol, sodium azide, and tert-butanol) that are commonly employed to study photodegradation mechanisms and kinetics. The carbon analog of EBS, namely, 2-phenyl-3H-isoindol-1-one, was included as a reference compound to confirm the impact of the selenium atom on EBS photochem. reactivity. EBS does not undergo acid dissociation, but pH-dependent kinetics were observed in RB-sensitized solutions, suggesting EBS reaction with active intermediates (³RB^2-*, O₂^闂?, and H₂O₂) that are not kinetically relevant for other compounds In addition, the observed rate constant of EBS increased in the presence of sorbic acid, isopropanol, and sodium azide. These findings suggest that conventional reactive species sensitizers, scavengers, and quenchers need to be carefully applied to highly reactive organoselenium compounds to account for reactions that are typically slow for other organic contaminants. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).}

Paintner, Franz F. et al. published their research in Synlett in 2002 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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-(Phenylthio)isoindoline-1,3-dione

Synthetic studies toward tetrodecamycin: an efficient approach to the core structure of the antibiotic was written by Paintner, Franz F.;Allmendinger, Lars;Bauschke, Gerd;Polborn, Kurt. And the article was included in Synlett in 2002.Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

An efficient synthetic pathway to the core structure I of the polyketide antibiotic tetrodecamycin has been developed. Our approach features the acid-catalyzed cyclization of a tert-butyldimethylsilyl protected Me 婵?(缂?hydroxyacyl) tetronate, leading to the novel tricyclic ring skeleton exhibited by I. An insight into the mechanism of this key ring closure step has been gained. Furthermore an alternative pathway to this ring skeleton, based on a fluoride ion induced desilylation-cyclization sequence, has been disclosed. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione).

Penthala, Narsimha Reddy et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2010 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. 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: C9H6ClNO

Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines was written by Penthala, Narsimha Reddy;Yerramreddy, Thirupathi Reddy;Crooks, Peter A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C9H6ClNO This article mentions the following:

The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. Several of these compounds were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC₅₀ values <10 濠电偞鎸鹃幏?for 30% of the cell lines in the panel. Compound 3e was an effective inhibitor of leukemia, CNS, melanoma, and breast cancer cell growth, but generally less effective as a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Formula: C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. 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: C9H6ClNO

Zaryanova, Ekaterina V. et al. published their research in Tetrahedron in 2017 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Application In Synthesis of 7-Nitroindoline-2,3-dione

Synthesis and reactivity of new amide-substituted oxindole derivatives was written by Zaryanova, Ekaterina V.;Ignatov, Alexander A.;Lozynskaya, Nataly A.. And the article was included in Tetrahedron in 2017.Application In Synthesis of 7-Nitroindoline-2,3-dione This article mentions the following:

A general approach to the synthesis of oxindole-based amides I (R = 5-NHC(O)OMe, 5-NHCOPh, 5-NHCOPh-7-NHCOMe, etc.) is described. To stabilize the aminoisatin mol. for further modifications, the carbonyl group in the 3-position of the starting nitroisatins was protected by conversion into a ketal. Next, the reduction of the nitro group and further acylation of the resulting amino group were carried out to provide the corresponding mono- and diamido-substituted isatins I. The possibility of their modification in the 3-position for the synthesis of potent biol. active compounds is demonstrated. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Application In Synthesis of 7-Nitroindoline-2,3-dione).