February 2023 - Page 109 of 117 - Indole Building Blocks

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).

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

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).

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).

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).

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).

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).

DeRatt, Lindsey G. et al. published their research in Organic Letters in 2019 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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.COA of Formula: C9H6BrNO2

Mild Intramolecular Ring Opening of Oxetanes was written by DeRatt, Lindsey G.;Lawson, Edward C.;Wang, Chao-Yuan;Kuduk, Scott D.. And the article was included in Organic Letters in 2019.COA of Formula: C9H6BrNO2 This article mentions the following:

Herein, an intramol. ring opening of oxetane carboxamides with mild nucleophiles, such as nitrogen heterocycles, is presented. The reaction proceeds under metal-free basic conditions which is highly unusual in ring opening reactions of oxetanes. Amide formation and oxetane ring opening/cyclization in a one-pot approach affords high levels of mol. complexity in a single step from simple, readily available substrates. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2COA of Formula: C9H6BrNO2).

Zhang, Chufeng et al. published their research in European Journal of Medicinal Chemistry in 2019 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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 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: C13H17BN2O2

Design, synthesis and evaluation of novel 7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives as potent, selective and reversible Bruton’s tyrosine kinase (BTK) inhibitors for the treatment of rheumatoid arthritis was written by Zhang, Chufeng;Pei, Heying;He, Jun;Zhu, Jiali;Li, Weimin;Niu, Ting;Xiang, Mingli;Chen, Lijuan. And the article was included in European Journal of Medicinal Chemistry in 2019.COA of Formula: C13H17BN2O2 This article mentions the following:

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives was designed and synthesized as reversible BTK inhibitors, and evaluated for their kinase selectivity, anti-proliferative activity against the B-cell lymphoma cell lines (Ramos, Jeko-1) and cell line BTK enhanced (Daudi) in vitro. Among them, pyrrolo[2,3-d]pyrimidine I exhibited the most excellent potency (IC₅₀ = 3.0 nM against BTK enzyme, 8.52 μM, 11.10 μM and 7.04 μM against Ramos, Jeko-1, Daudi cells, resp.), good kinase selectivity and inhibited BTK Y223 auto-phosphorylation and PLCγ2 Tyr1217 phosphorylation. Importantly, the compound I showed effective anti-arthritic effect on collagen-induced arthritis (CIA) model in vivo. 60 Mg/kg dose level once a day group displayed markedly reduced joint damage and cellular infiltration without any bone and cartilage morphol. change. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7COA of Formula: C13H17BN2O2).

Wilk, Wolfram et al. published their research in Chemistry – A European Journal in 2009 | 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. 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: C9H6ClNO

Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection was written by Wilk, Wolfram;Noeren-Mueller, Andrea;Kaiser, Markus;Waldmann, Herbert. And the article was included in Chemistry – A European Journal in 2009.Formula: C9H6ClNO This article mentions the following:

Macrolines constitute a class of natural products that has more than 100 members and displays diverse biol. activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biol.-oriented synthesis (BIOS). We have presented a solid-phase synthesis of isomerically pure cycloocta[b]indoles (e.g. I) by employing the Pictet-Spengler reaction and the Dieckmann cyclization as key steps. The scope of this reaction sequence was investigated in more detail by using various addnl. diversification procedures, such as Pd-catalyzed Sonogashira or Suzuki couplings on a solid phase, thus allowing, for example, the generation of 10-substituted cycloocta[b]indole derivatives Finally, solution-phase decoration of the cycloocta[b]indole skeleton by reduction and saponification was evaluated, thereby further extending the scope of the solid-phase synthesis. 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, 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. 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: C9H6ClNO

Chang, Yu-Hsuan et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2020 | 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Safety of 5-Chloroindole-3-carboxaldehyde

Palladium-catalyzed α-arylation of indolin-3-ones was written by Chang, Yu-Hsuan;Peng, Wan-Ling;Chen, I-Chia;Hsu, Hsin-Yun;Wu, Yen-Ku. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)₂ and PAd₃ was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).