indole-building-block | - Page 110 of 1434

Nikpour, Farzad et al. published their research in Heterocycles in 2006 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Category: indole-building-block

A facile and convenient synthesis of 1H-isoindole-1,3(2H)-diones was written by Nikpour, Farzad;Kazemi, Samira;Sheikh, Davood. And the article was included in Heterocycles in 2006.Category: indole-building-block This article mentions the following:

A facile synthesis of 1H-isoindole-1,3(2H)-diones (e.g., I) has been developed by the reaction of the corresponding anhydrides (e.g., II) with potassium cyanate or sodium thiocyanate. The reactions were carried out in neutral media under reflux or under microwave irradiation without use of catalyst. Good to excellent yields of the products were obtained in high purity with very simple work-up. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Category: indole-building-block).

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

Russell, Glen A. et al. published their research in Journal of the American Chemical Society in 1997 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Safety of 2-(Phenylthio)isoindoline-1,3-dione

Homolytic Base-Promoted Aromatic Alkylations by Alkylmercury Halides was written by Russell, Glen A.;Chen, Ping;Kim, Byeong Hyo;Rajaratnam, Ragine. And the article was included in Journal of the American Chemical Society in 1997.Safety of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Electron transfer chain reactions leading to substitution in electronegatively substituted benzene derivatives can be observed with alkylmercury halides in the presence of proton acceptors such as DABCO. Promotion by base involves the abstraction of a proton from the substituted cyclohexadienyl adduct radical to form a radical anion which readily transfers an electron to RHgX with the regeneration of Râ? Aromatic substitutions involving Me₃Câ?are highly regioselective and yield products of only para attack for PhCHO, PhCOMe, PhCOCMe₃, PhCOPh, PhCN, phthalimides, or 1,2-dicyanobenzene. The ortho/para substitution products are observed for isophthalaldehyde or 1,3-dicyanobenzene, while 1,4-dicyanobenzene yields the ortho substitution product. At 25-35Â° substitution by Me₃Câ?ortho to an ester group is not observed and m- or p-cyanobenzoate esters yield only products of substitution ortho to the cyano group. With Me₂CHâ?substitution ortho to the ester function is observed with di-Et isophthalate. Intramol. radical cyclizations of the radical adducts of 1-aryl-4-penten-1-ones leading to Î±-tetralones is also promoted by the presence of DABCO. When the aryl group contains a para ester function, spirocyclization occurs leading to a rearrangement acyl radical which can be oxidized by Me₃CHgCl to the acyl cation and the carboxylic acid. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Safety of 2-(Phenylthio)isoindoline-1,3-dione).

Ranasinghe, Nadeesha et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2013 | 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. 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). Safety of Methyl 5-fluoro-1H-indole-2-carboxylate

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry was written by Ranasinghe, Nadeesha;Jones, Graham B.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Safety of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

Microwave, flow and combination methodologies were applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodol. allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chem., allowing formation of peptide adducts which can be subsequently labeled with fluorine tags. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Safety of Methyl 5-fluoro-1H-indole-2-carboxylate).

Wu, Ge et al. published their research in Organic Letters in 2013 | CAS: 827-01-0

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

Regio- and Stereoselective Direct N-Alkenylation of Indoles via Pd-Catalyzed Aerobic Oxidation was written by Wu, Ge;Su, Weiping. And the article was included in Organic Letters in 2013.Computed Properties of C9H6ClNO This article mentions the following:

With two different sets of Pd catalyst systems in hand, indoles, whether bearing a C3-substituent or not, can be directly alkenylated on their nitrogen atoms using a sterically and electronically diverse array of alkenes, in which the high regio- and stereoselectivity are dependent on the nature of the alkenes used. This process proceeds in generally good yields and is compatible with a broad range of functional groups. Thus, a large series of N-alkenylated indoles, e.g., I, has been prepared In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).

Yamamoto, Iwao et al. published their research in Tetrahedron Letters in 1971 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Computed Properties of C14H11NO

Reaction of isocyanate with phthalaldehyde was written by Yamamoto, Iwao;Tabo, Yoshizo;Gotoh, Haruo;Minami, Toru;Ohshiro, Yoshiki;Agawa, Toshio. And the article was included in Tetrahedron Letters in 1971.Computed Properties of C14H11NO This article mentions the following:

Phthalimidines (I) are prepared by the reaction of phthalaldehyde (II) with aryl isocyanates ArNCO. Thus, an equimolar mixture of PhNCO and II is heated to give N-phthalimidine (III). Similarly prepared are I (Ar = o-tolyl, m-ClC6H4, o-ClC6H4). Probably, IV are intermediates. II is treated with PhN:C:NPh to give III. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Computed Properties of C14H11NO).

Proctor, G. R. et al. published their research in Journal of the Chemical Society in 1972 | 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.SDS of cas: 5388-42-1

Azocine derivatives. I. Synthesis of 1-benzazocin-6-one derivatives by direct cyclization was written by Proctor, G. R.;Ross, W. I.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1972.SDS of cas: 5388-42-1 This article mentions the following:

Treatment of o-MeO2CC6H4NHSO2C6H4Me-p with Br(CH2)4CO2Et followed by NaH in DMF gave Et 1,2,3,4,5, 6-hexahydro-6-oxo-N-(p-tolylsulfonyl)-1-benzazocine-5-carboxylate (I, R = CO2Et) by Dieckmann cyclization. Acid hydrolysis of I (R = CO2Et) gave 2,3,4,6-tetrahydro-N-(p-tolylsulfonyl)-1-benzazocin-6(1H)-one (I, R = H) in 30% overall yield. NaBH4 reduction of I (R = H) gave the corresponding alc., which with Na-liquid NH3 gave 1,2,3,4,5,6-hexahydro-1-benzazocin-6-ol. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

Song, Jiahui et al. published their research in Asian Journal of Organic Chemistry in 2013 | CAS: 1256359-99-5

tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C20H28BNO5

Copper-Catalyzed N-Alkynylation of N-tert-Butoxycarbonyl (BOC)-Protected Indoles was written by Song, Jiahui;Wang, Qingbo;Fu, Haixing;Fu, Songlin;Li, Shaobin;Shi, Feng;Wu, Chunrui. And the article was included in Asian Journal of Organic Chemistry in 2013.Computed Properties of C20H28BNO5 This article mentions the following:

N-BOC-indole derivatives undergo a copper-catalyzed N-alkynylation with alkynyl bromides after in situ deprotection. Potassium tert-butoxide was used for the deprotection of substrates and as a base during the cross-coupling stage. For substrates that contain a 2-pyridine group or similar group, a phenanthroline ligand was not needed. This serves as an alternative protocol for N-alkynylation of indoles with a broader scope of substrates. The title compounds thus formed included an (ethynyl)indole derivative (I) and related substances. The synthesis of the target compounds was achieved using 3-(2-pyridinyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, 5-(2-pyridinyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, 1H-Indole-1,2-dicarboxylic acid 1,2-bis(1,1-dimethylethyl) ester, 4-cyano-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, etc., as starting materials in a reaction with bromoalkyne derivatives A similar reaction of 1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester gave 1-(2-phenylethynyl)-1H-benzimidazole. A reaction of 1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester derivatives gave 1-(2-phenylethynyl)-1H-pyrrole derivatives In the experiment, the researchers used many compounds, for example, tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5Computed Properties of C20H28BNO5).

Romagnoli, Romeo et al. published their research in Letters in Drug Design & Discovery in 2009 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. 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: C10H8FNO2

Discovery of 8-methoxypyrazino[1,2-a]indole as a new potent antiproliferative agent against human leukemia K562 cells. a structure-activity relationship study was written by Romagnoli, Romeo;Baraldi, Pier Giovanni;Carrion, Maria Dora;Cruz-Lopez, Olga;Cara, Carlota Lopez;Preti, Delia;Tabrizi, Mojgan Aghazadeh;Balzarini, Jan;Hamel, Ernest;Fabbri, Enrica;Gambari, Roberto. And the article was included in Letters in Drug Design & Discovery in 2009.Formula: C10H8FNO2 This article mentions the following:

Identification of novel and selective anticancer agents remains an important and challenging goal in pharmacol. research. The indole nucleus, frequently encountered as a mol. fragment in natural products and pharmaceutically active compounds, was employed as the initial building block for the synthesis of a series of pyrazino[1,2-a]indoles 1a-k, variably substituted at the 6, 7, 8 and 9-positions. Compound 1e (I), bearing the methoxy group at the 8-position of the pyrazino[1,2-a]indole nucleus was identified as a novel potent antiproliferative agent against the human chronic myelogenous leukemia K562 cell line, but it was much less active against several other cancer cell lines. Comparison of positional isomers indicated that moving the methoxy group from the 8- to the 7- or 6-position, to furnish compounds 1f and 1g, resp., yielded inactive compounds The anal. of structure-activity relationships observed in the series of investigated compounds may represent the basis for the design of more active mols. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Formula: C10H8FNO2).

Singha Roy, Soumya Jyoti et al. published their research in Organic & Biomolecular Chemistry in 2017 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Computed Properties of C14H9NO2S

“On water” catalytic enantioselective sulfenylation of deconjugated butyrolactams was written by Singha Roy, Soumya Jyoti;Mukherjee, Santanu. And the article was included in Organic & Biomolecular Chemistry in 2017.Computed Properties of C14H9NO2S This article mentions the following:

In the presence of phthalazine-linked quinidine or quinine dimers, deconjugated γ-butenolactams such as racemic I (R = H) underwent enantioselective arylsulfenylation and phenylselenenylation reactions with arylthio- and phenylselenosuccinimides in tert-butylbenzene/water mixtures to yield nonracemic α-arylthio- and α-phenylselenenobutenolactams such as I (R = PhS, PhSe) in 56-94% yields and in 47->96% ee; a lactam with an α-iso-Pr substituent and benzylthiol- and cyclohexanethiol-derived succinimides did not yield sulfenylation products. Oxidation and rearrangement of I (R = PhSe) yielded a nonracemic γ-hydroxybutenolactam by formal γ-hydroxylation; the selenylation and hydroxylation reactions were performed in tandem. The structures of I (R = PhS, PhSe) and of the oxidation and rearrangement product of I (R = PhSe) were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Computed Properties of C14H9NO2S).

Kilic-Kurt, Zuehal et al. published their research in Archiv der Pharmazie (Weinheim, Germany) in 2020 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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 167631-84-7

Novel indole hydrazide derivatives: Synthesis and their antiproliferative activities through inducing apoptosis and DNA damage was written by Kilic-Kurt, Zuehal;Acar, Cemre;Ergul, Mustafa;Bakar-Ates, Filiz;Altuntas, Tunca G.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2020.Product Details of 167631-84-7 This article mentions the following:

A series of novel indole hydrazide derivatives was synthesized and evaluated for their anticancer activities. Compound 12(I) exhibited the highest antiproliferative activity against the MCF-7 cell line, with an IC₅₀ value of 3.01μM. Treatment of MCF-7 cells with compound 12 led to cell cycle arrest at the G0/G1 phase and also displayed a significant annexin V binding pattern, indicating that compound 12 is effective in apoptotic cell death. The Western blot anal. showed that compound 12 increased the expression of proapoptotic Bax and decreased the levels of the antiapoptotic Bcl-2 protein. It was also observed that MCF-7 cells treated with compound 12 showed reduced levels of procaspase-3 and -9 proteins. Moreover, compound 12 treatment induced a significant DNA damage in MCF-7 cells by increasing H2AX and ATM phosphorylation. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Product Details of 167631-84-7).