136818-52-5Relevant articles and documents
Ligand-free copper-catalyzed one-pot synthesis of indole-2-carboxylic esters
Zhu, Zhiqiang,Yuan, Jiangjun,Zhou, Yirong,Qin, Yang,Xu, Jingshi,Peng, Yiyuan
supporting information, p. 511 - 514 (2014/02/14)
A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu 2O and a base to provide the corresponding products in good yields. Commercially available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles. A simple, efficient, and facile synthetic route to indole-2-carboxylic esters through copper-catalyzed one-pot cascade reactions of commercially available, inexpensive 2-bromobenzaldehyde and glycine ester hydrochloride without the use of any external ligand under mild conditions is reported. Copyright
Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters
Zhu, Zhiqiang,Yuan, Jiangjun,Zhou, Yirong,Qin, Yang,Xu, Jingshi,Peng, Yiyuan
supporting information, p. 511 - 514 (2015/10/05)
A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu2O and a base to provide the corresponding products in good yields. Commercially available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles.
Gold(I)-catalyzed rearrangement of alkynylaziridine indoles for the synthesis of spiro-tetrahydro-β-carbolines
Yang, Yan-Fang,Li, Lian-Hua,He, Yu-Tao,Luo, Jian-Yi,Liang, Yong-Min
, p. 702 - 707 (2014/02/14)
Functionalized spiro-tetrahydro-β-carbolines were formed by an efficient gold(I)-catalyzed rearrangement reaction of alkynylaziridine indoles. The reaction involved a Friedel-Crafts type intramolecular reaction of alkynylaziridine indoles, following by hydroamination of aminoallene intermediate.
Iron(II) triflate as a catalyst for the synthesis of indoles by intramolecular C-H amination
Bonnamour, Julien,Bolm, Carsten
, p. 2012 - 2014 (2011/06/28)
A practical iron-catalyzed intramolecular C-H amination reaction and its application in the synthesis of indole derivatives are presented. As a catalyst, commercially available iron(II) triflate is used.
[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source
Liu, Yungen,Wei, Jinhu,Che, Chi-Ming
supporting information; experimental part, p. 6926 - 6928 (2010/11/16)
The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.
Tandem palladium-catalyzed N,C-coupling/carbonylation sequence for the synthesis of 2-carboxyindoles
Vieira, Tiago O.,Meaney, Laura A.,Shi, Yong-Ling,Alper, Howard
supporting information; experimental part, p. 4899 - 4901 (2009/05/31)
(Chemical Equation Presented) Tandem palladium-catalyzed N,C-coupling/carbonylation, under 10 aim of carbon monoxide and at 110 °C, is a novel and efficient method for the preparation of 2-carboxyindoles. The catalyst system tolerates a variety of functional groups, and the noted indoles were obtained in good isolated yields.
Hyperbranched molecular structures with potential antiviral activity: Derivatives of 5,6-dihydroxyindole-2-carboxylic acid
Sechi, Mario,Casu, Fabio,Campesi, Ilaria,Fiori, Stefano,Mariani, Alberto
, p. 968 - 977 (2007/10/03)
In the search of new HIV-1 integrase (IN) inhibitors, we synthesized a series of multimeric 5,6-dihydroxyindole-2-carboxylic acid (DHICA) derivatives. Preliminary results indicate that hyperbranched architectures could represent a peculiar molecular requi
CBI analogues of the duocarmycins and CC-1065
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Page 30, (2010/02/10)
An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be ≧1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC50=2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065. The increases in cytotoxicity correlate well with accompanying increases in the rate and efficiency of DNA alkylation. This effect is more pronounced with the CBI versus DSA or CPI based analogues. Moreover, this effect is largely insensitive to the electronic character of the C5 substituent but is sensitive to the size, rigid length, and shape (sp, sp2, sp3 hybridization) of this substituent consistent with expectation that the impact is due simply to its presence.
Design and synthesis of novel indole β-diketo acid derivatives as HIV-1 integrase inhibitors
Sechi, Mario,Derudas, Massimiliano,Dallocchio, Roberto,Dessì, Alessandro,Bacchi, Alessia,Sannia, Luciano,Carta, Fabrizio,Palomba, Michele,Ragab, Omar,Chan, Carney,Shoemaker, Robert,Sei, Shizuko,Dayam, Raveendra,Neamati, Nouri
, p. 5298 - 5310 (2007/10/03)
Diketo acids such as S-1360 (1A) and L-731,988 (2) are potent and selective inhibitors of HIV-1 integrase (IN). A plethora of diketo acid-containing compounds have been claimed in patent literature without disclosing much biological activities and synthetic details (reviewed in Neamati, N. Exp. Opin. Ther. Pat. 2002, 12, 709-724). To establish a coherent structure - activity relationship among the substituted indole nucleus bearing a β-diketo acid moiety, a series of substituted indole-β-diketo acids (4a-f and 5a-e) were synthesized. All compounds tested showed anti-IN activity at low micromolar concentrations with varied selectivity against the strand transfer process. Three compounds, the indole-3-β-diketo acids 5a and 5c, and the parent ester 9c, have shown an antiviral activity in cell-based assays. We further confirmed a keto-enolic structure in the 2,3-position of the diketo acid moiety of a representative compound (4c) using NMR and X-ray crystallographic analysis. Using this structure as a lead for all of our computational studies, we found that the title compounds extensively interact with the essential amino acids on the active site of IN.
Anti-aids piperazines
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, (2008/06/13)
The present invention includes diaromatic substituted heterocyclic compounds (III) STR1 which are useful in treating individuals infected with the HIV virus. The invention includes certain previously generically disclosed anti-AIDS piperazinyl compounds (V) and a method of treating HIV infected individuals with the indoles of formula (V) and the anti-AIDS amines (X).
