04/01/2023 - Page 3 of 11 - Indole Building Blocks

Fujita, Hiroshi et al. published their research in Chemical & Pharmaceutical Bulletin in 1975 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Name: 2-Phenylisoindolin-1-one

Synthetic studies on 2,4-benzothiazepin-5(1H)-one and 2,4-benzodiazepin-1-one derivatives was written by Fujita, Hiroshi;Sato, Yasunobu. And the article was included in Chemical & Pharmaceutical Bulletin in 1975.Name: 2-Phenylisoindolin-1-one This article mentions the following:

2,4-Benzothiazepin-5(1H)-ones were usually the predominant products in reactions of o-chloromethylbenzoyl chloride with 1,3-disubstituted thioureas; but with methyl, benzyl or allyl substituted thioureas, 2,4-benzodiazepin-1-ones were obtained together with 2,4-benzothiazepin-5(1H)-ones. These structures were elucidated from NMR spectra. The nature of the base and solvent as well as thiourea substituents affected the course of the reactions affording 2,4-benzothiazepin-5(1H)-ones or 2,4-benzodiazepin-1-ones. Several 2,4-benzothiazepin-5(1H)-ones and 2,4-benzodiazepin-1-ones possessed weak pharmacological activities, such as coronary vasodilating and local anesthetic activity. 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 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

Reddy, Yervala D. et al. published their research in Letters in Organic Chemistry in 2013 | 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.COA of Formula: C8HBr4NO2

A facile and green synthesis of novel imide and amidic acid derivatives of phenacetin as potential analgesic and anti-pyretic agents was written by Reddy, Yervala D.;Kumar, Padam P.;Devi, Bhoomireddy R.;Dubey, Pramod K.;Kumari, Yalamanchili B.. And the article was included in Letters in Organic Chemistry in 2013.COA of Formula: C8HBr4NO2 This article mentions the following:

Facile and green syntheses of potential analgesic and antipyretic compounds, N-(4-ethoxyphenyl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)acetamide derivatives and N-[(4-ethoxyphenylcarbamoyl)methyl]phthalamic acid derivatives have been developed. Two synthetic routes (A and B) have been established for the preparation of the former. In the route-A, 4-ethoxyaniline was reacted with chloroacetyl chloride in a solution of potassium acetate and acetic acid to yield N-(4-ethoxyphenyl)-2-chloroacetamide. The latter was reacted with imide compounds either in triethanolamine as a green solvent or in solid phase in the presence of TEBAC and KI to yield the products. Alternatively, in the route-B, reaction of anhydrides with glycine yielded the (1,3-dioxo-1,3-dihydroisoindol-2-yl)acetic acid derivatives which on reaction with 4-ethoxyaniline either in triethnolamine and DCC as a dehydrating agent or in solid phase in the presence of DCC gave the products. The latter were hydrolyzed in 0.5N ethanolic KOH to afford N-[(4-ethoxyphenylcarbamoyl)methyl]phthalamic acid derivatives In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7COA of Formula: C8HBr4NO2).

Tsuritani, Takayuki et al. published their research in Synlett in 2006 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Reference of 5388-42-1

A short and efficient synthesis of isoindolin-1-ones was written by Tsuritani, Takayuki;Kii, Satoshi;Akao, Atsushi;Sato, Kimihiko;Nonoyama, Nobuaki;Mase, Toshiaki;Yasuda, Nobuyoshi. And the article was included in Synlett in 2006.Reference of 5388-42-1 This article mentions the following:

A short and efficient synthesis of isoindolin-1-ones is reported. Base-induced cyclization of ortho-(hydroxymethyl)benzamides, which were easily prepared from the corresponding phthalides and amines, led predominantly to N-alkylation in good yield. The reaction proceeded under mild conditions and bromine and nitrile substituents were tolerated. The selectivity is explained by HASB theory. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Reference of 5388-42-1

Pan, Yue et al. published their research in Organic Letters in 2022 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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.SDS of cas: 4769-96-4

Hypervalent Iodine Reagents Enable C(sp²)-H Amidation of (Hetero)arenes with Iminophenylacetic Acids was written by Pan, Yue;Liu, Zhengyi;Zou, Peng;Chen, Yali;Chen, Yiyun. And the article was included in Organic Letters in 2022.SDS of cas: 4769-96-4 This article mentions the following:

The sulfonamidyl (hetero)arenes synthesis by the C(sp²)-H amidation from bench-stable amidyl-iminophenylacetic acids was reported. The hypervalent iodine reagents covalently activated iminophenylacetic acids for the facile sulfonamidyl radical generation under mild photocatalytic oxidative conditions. Diversified indoles, pyrroles, imidazopyridines and fused arenes underwent the C(sp²)-H amidation with excellent chemoselectivity and regioselectivity. This reaction performed well under neutral aqueous conditions with potential biol. applications. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4SDS of cas: 4769-96-4).

Zhang, Tao et al. published their research in Organic Letters in 2019 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Safety of 5-Chloroindole-3-carboxaldehyde

Pd(II)-Catalyzed Asymmetric Oxidative Annulation of N-Alkoxyheteroaryl Amides and 1,3-Dienes was written by Zhang, Tao;Shen, Hong-Cheng;Xu, Jia-Cheng;Fan, Tao;Han, Zhi-Yong;Gong, Liu-Zhu. And the article was included in Organic Letters in 2019.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The first Pd(II)-catalyzed asym. oxidative annulation of N-alkoxyaryl amides and 1,3-dienes is reported, which features particular applicability for quick assembly of different types of chiral heterocycles with high yields and enantioselectivities. A novel chiral pyridine-oxazoline bearing a methoxyl group at the C-5 position and a gem-di-Me group on the oxazoline moiety was found to be crucial for conversion. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

Lombardi, Lorenzo et al. published their research in Chemistry – A European Journal in 2020 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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.Product Details of 4583-55-5

Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode was written by Lombardi, Lorenzo;Bellini, Daniele;Bottoni, Andrea;Calvaresi, Matteo;Monari, Magda;Kovtun, Alessandro;Palermo, Vincenzo;Melucci, Manuela;Bandini, Marco. And the article was included in Chemistry – A European Journal in 2020.Product Details of 4583-55-5 This article mentions the following:

The site-selective allylative and allenylative dearomatization of indoles with alcs. was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt % loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H₂O/CH₃CN, 55 C, 6 h), broad substrate scope (33 examples, yield up to 92%) and excellent site- and stereoselectivity characterize the present methodol. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, exptl. and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Product Details of 4583-55-5).

Denmark, Scott E. et al. published their research in Nature Chemistry in 2014 | CAS: 14204-27-4

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

Mechanistic, crystallographic, and computational studies on the catalytic, enantioselective sulfenofunctionalization of alkenes was written by Denmark, Scott E.;Hartmann, Eduard;Kornfilt, David J. P.;Wang, Hao. And the article was included in Nature Chemistry in 2014.Product Details of 14204-27-4 This article mentions the following:

The stereocontrolled introduction of vicinal heteroat. substituents into organic mols. is one of the most powerful ways of adding value and function. Although many methods exist for the introduction of oxygen- and nitrogen-containing substituents, the number of stereocontrolled methods for the introduction of sulfur-containing substituents pales by comparison. Previous reports from our laboratories have described sulfenofunctionalizations of alkenes that construct carbon-sulfur bonds vicinal to carbon-oxygen, carbon-nitrogen or carbon-carbon bonds with high levels of diastereospecificity and enantioselectivity. This process is enabled by the concept of Lewis-base activation of Lewis acids, which provides activation of Group 16 electrophiles. To provide a foundation for the expansion of substrate scope and improved selectivities, we have undertaken a comprehensive study of the catalytically active species. Insights gleaned from kinetic, crystallog. and computational methods have led to the introduction of a new family of sulfenylating agents that provide significantly enhanced selectivities. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Product Details of 14204-27-4).

Dysz, Karolina et al. published their research in Polyhedron in 2019 | CAS: 1000340-39-5

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Safety of 3-Bromo-4-chloro-7-azaindole

A comparative study on cisplatin analogs containing 7-azaindole (7AIH) and its seven halogeno-derivatives: Vibrational spectra, DFT calculations and in vitro antiproliferative activity. Crystal and molecular structure of cis-[PtCl₂(4Br7AIH)₂]·DMF was written by Dysz, Karolina;Szmigiel-Bakalarz, Ksenia;Nentwig, Markus;Oeckler, Oliver;Malik-Gajewska, Magdalena;Turlej, Eliza;Michalska, Danuta;Morzyk-Ociepa, Barbara. And the article was included in Polyhedron in 2019.Safety of 3-Bromo-4-chloro-7-azaindole This article mentions the following:

Eight platinum(II) complexes of the general formula cis-[PtCl₂(L)₂] containing 7-azaindole (L = 7AIH) and its halogeno-derivatives: L = 3-chloro-7-azaindole (3Cl7AIH); 3-bromo-7-azaindole (3Br7AIH); 4-chloro-7-azaindole (4Cl7AIH); 4-bromo-7-azaindole (4Br7AIH); 5-bromo-7-azaindole (5Br7AIH); 3-bromo-4-chloro-7-azaindole (3Br4Cl7AIH) and 5-bromo-3-chloro-7-azaindole (5Br3Cl7AIH) were prepared Two complexes, cis-[PtCl₂(3Br4Cl7AIH)₂] (2) and cis-[PtCl₂(4Br7AIH)₂]·DMF, are reported for the first time. Crystal structure of the latter compound has been determined with x-ray diffraction anal. (space group P4₃, with a = 14.775(2), c = 41.640(8) Å, V = 9090(3) Å³ and Z = 16). For all of these complexes, formation of the cis isomers in the solid state was confirmed by exptl. vibrational (IR and Raman) spectroscopy combined with DFT calculations A complete assignment of the IR and Raman spectra was made on the basis of the calculated potential energy distribution (PED). Stability of complex (2) in DMSO solution was investigated by FT-IR (ATR) spectroscopy. The in vitro antiproliferative activity of cis-[PtCl₂(3Br4Cl7AIH)₂], cis-[PtCl₂(3Cl7AIH)₂] and cis-[PtCl₂(3Br7AIH)₂] was evaluated on selected human cancer cell lines and towards normal mouse fibroblast cell line (BALB/3T3). All complexes are more toxic than cisplatin against Es-2 (ovarian cancer), LNCaP (prostate adenocarcinoma) and MCF7 (breast cancer). Moreover, complex (2) is significantly more active than the other complexes on A549 (lung carcinoma, IC₅₀ = 3.9 μM). However, the three investigated Pt(II) complexes with 7-azaindoles have revealed higher cytotoxicity against a normal cell line (BALB/3T3), in comparison to cisplatin. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Safety of 3-Bromo-4-chloro-7-azaindole).

Dethe, Dattatraya H. et al. published their research in European Journal of Organic Chemistry in 2018 | CAS: 89245-41-0

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Name: 4-Bromoindole-3-acetic Acid

Rapid One-Pot Access to Unique 3,4-Dihydrothiopyrano[3,4-b]indol-1(9H)-imines via Bi(OTf)₃-Catalysed Tandem Friedel-Crafts Alkylation/Thia-Michael Addition was written by Dethe, Dattatraya H.;Boda, Vijay Kumar;Mandal, Anupam. And the article was included in European Journal of Organic Chemistry in 2018.Name: 4-Bromoindole-3-acetic Acid This article mentions the following:

A highly efficient and atom economical one-pot annulation strategy for tetrahydrothiopyrano[3,4-b]indoles, e.g., I, is presented. This protocol involves a Bi(OTf)₃ catalyzed tandem Friedel-Crafts alkylation and intramol. thia-Michael addition reactions to furnish target mols. in an efficient manner. The method works effectively on substrates with unprotected indoles and also it is successfully employed to make tetrahydrothiepino[3,4-b]indoles. The scaffolds synthesized are diverse and first of the kind. The reaction is practically simple with broad substrate scope and vast functional group compatibility. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Name: 4-Bromoindole-3-acetic Acid).

Lai, Huifang et al. published their research in Organic & Biomolecular Chemistry in 2021 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.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

Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate was written by Lai, Huifang;Xu, Jiexin;Lin, Jin;Zha, Daijun. And the article was included in Organic & Biomolecular Chemistry in 2021.Category: indole-building-block This article mentions the following:

Isoindolinones are ubiquitous structural motifs in natural products and pharmaceuticals. Establishing an efficient method for structural modification of isoindolinones could significantly facilitate new drug development. Herein, authors describe copper-promoted direct amidation of isoindolinone scaffolds mediated by sodium persulfate. The method exhibits mild reaction conditions and high site-selectivity, and enables the structural modification of the drug indobufen ester with various amides with yields of 49 to 98%. It is also gram-scalable. Addnl., the reaction mechanism appears to involve a radical and a carbocationic pathway. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Category: indole-building-block).