- Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds to Form Highly Functionalized Carbazoles
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A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a novel [5 + 1] cyclization product with good to excellent yields (up to 95%), accompanied by the thorough removal of acetyl and N,N-dimethyl groups of two substrates from the target products, rather than the normally expected [4 + 2] cyclization products.
- Jiang, Zhidong,Liu, Hong,Zhou, Jianhui,Zhou, Yu,Zhu, Haoran
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supporting information
p. 4406 - 4410
(2021/06/28)
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- Cascade Reaction to Selectively Synthesize Multifunctional Indole Derivatives by IrIII-Catalyzed C?H Activation
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An effective and condition-controlled way to synthesize with high selectivity a variety of functionalized indoles with potent biological properties has been developed. Notably, 2,4-dialkynyl indole products were obtained by direct double C?H bond alkynylation, whereas alkynyl at the C4 position could convert to carbonyl to generate 2-alkynyl-3,4-diacetyl indoles fast and effectively. Additionally, a one-pot relay catalytic reaction led to 2,5-di-alkynyl-3,4-diacetyl indoles when using a carbonyl group as the directing group and by controlling the type and quantity of additives. A possible mechanism was proposed based on many studies including deuterium-exchange experiments, the necessary conditions of product conversion, and the effect of water on the reaction.
- Chai, Xin-Yue,Xu, Hui-Bei,Dong, Lin
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supporting information
p. 13123 - 13127
(2021/08/13)
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- Natural product Pimprinine derivative as well as preparation method and application thereof
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The invention discloses a Pimprinine derivative as shown in a formula III in the description. The invention also discloses a preparation method of the Pimprinine derivative, and a series of Pimprinine derivatives are synthesized by taking Pimprinine as a lead, combining the structural characteristics of Pimprinine, taking cheap and easily available indole as a raw material, modifying and transforming different sites of a framework structure of the indole and introducing different substituent groups. The Pimprinine derivative disclosed by the invention has good bactericidal activity, shows efficient and/or broad-spectrum bactericidal activity, and can be applied to crop diseases caused by fungi, bacteria and viruses.
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Paragraph 0079-0082; 0084
(2021/07/31)
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- NbCl5 and AgClO4 promoted regio-selective acylation of indoles
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In present study, an efficient and simple strategy towards chemo-selective and regio-selective acylation of indole using NbCl5 and AgClO4 catalyst are reported. This method utilizes the catalytic potentiality of NbCl5 and AgClO4 towards acylation of unprotected indoles in a synergistic manner. The combination of these catalytic system results into numerous advantages such as excellent yields of product, short reaction times and easier isolation of products.
- Kamble, Narendra R.,Pawar, Hari R.,Kamble, Vinod T.
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p. 317 - 321
(2020/01/08)
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- SMAC MIMETICS USED AS IAP INHIBITORS AND USE THEREOF
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Disclosed are a class of SMAC mimetics used as IAP inhibitors, and in particular disclosed are compounds as shown in formula (I), isomers thereof, and pharmaceutically acceptable salts thereof. The IAP inhibitors are drugs for treating cancers, in particu
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Paragraph 0069; 0070
(2020/12/10)
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- Expanding the SAR of Nontoxic Antiplasmodial Indolyl-3-ethanone Ethers and Thioethers
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Despite major strides in reducing Plasmodium falciparum infections, this parasite still accounts for roughly half a million annual deaths. This problem is compounded by the decreased efficacy of artemisinin combination therapies. Therefore, the development and optimisation of novel antimalarial chemotypes is critical. In this study, we describe our strategic approach to optimise a class of previously reported antimalarials, resulting in the discovery of 1-(5-chloro-1H-indol-3-yl)-2-[(4-cyanophenyl)thio]ethanone (13) and 1-(5-chloro-1H-indol-3-yl)-2-[(4-nitrophenyl)thio]ethanone (14), whose activity was equipotent to that of chloroquine against the P. falciparum 3D7 strain. Furthermore, these compounds were found to be nontoxic to HeLa cells as well as being non-haemolytic to uninfected red blood cells. Intriguingly, several of our most promising compounds were found to be less active against the isogenic NF54 strain, highlighting possible issues with long-term dependability of malarial strains. Finally compound 14 displayed similar activity against both the NF54 and K1 strains, suggesting that it inhibits a pathway that is uncompromised by K1 resistance.
- Lunga, Mayibongwe J.,Chisango, Ruramai L.,Weyers, Carli,Isaacs, Michelle,Taylor, Dale,Edkins, Adrienne L.,Khanye, Setshaba D.,Hoppe, Heinrich C.,Veale, Clinton G. L.
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p. 1353 - 1362
(2018/07/13)
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- Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria
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In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.
- Huggins, William M.,Barker, William T.,Baker, James T.,Hahn, Nicholas A.,Melander, Roberta J.,Melander, Christian
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p. 702 - 707
(2018/06/04)
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- Indole derivatives and their preparation method and anti-influenza virus effects
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The invention relates to the field of pharmaceutical chemistry and discloses novel indole compounds represented by the general formulas I, II and III and their preparation method, anti-influenza virus effects and good anti-influenza virus activity especia
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Paragraph 0065
(2017/10/13)
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- Br?nsted acidic ionic liquid-promoted direct C3-acylation of: N -unsubstituted indoles with acid anhydrides under microwave irradiation
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A green and efficient pathway for the synthesis of 3-acylindoles using a Br?nsted acidic ionic liquid as a catalyst has been developed for the first time. The C3-acylation of N-unsubstituted indoles with acid anhydrides affords the desired products in good to excellent yields with high regioselectivity under microwave irradiation. Moreover, the Br?nsted acidic ionic liquid can be recycled up to four times without significant loss of catalytic activity.
- Tran, Phuong Hoang,Duy Nguyen, Anh-Thanh,Nguyen, Hai Truong,Le, Thach Ngoc
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p. 54399 - 54406
(2017/12/12)
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- A simple, effective, green method for the regioselective 3-acylation of unprotected indoles
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A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.
- Tran, Phuong Hoang,Tran, Hai Ngoc,Hansen, Poul Erik,Do, Mai Hoang Ngoc,Le, Thach Ngoc
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p. 19605 - 19619
(2015/11/27)
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- A new potential approach to block HIV-1 replication via protein-protein interaction and strand-transfer inhibition
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Therapeutic treatment of AIDS is recently characterized by a crescent effort towards the identification of multiple ligands able to target different steps of HIV-1 life cycle. Taking into consideration our previously obtained SAR information and combining some important chemical structural features we report herein the synthesis of novel benzyl-indole derivatives as anti-HIV agents. Through this work we identified new dual target small molecules able to inhibit both IN-LEDGF/p75 interaction and the IN strand-transfer step considered as two crucial phases of viral life cycle.
- Ferro, Stefania,De Luca, Laura,Lo Surdo, Giuseppa,Morreale, Francesca,Christ, Frauke,Debyser, Zeger,Gitto, Rosaria,Chimirri, Alba
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p. 2269 - 2279
(2014/04/17)
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- Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-indol-3-yl)-4- phenylpyridine derivatives in vitro
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A series of novel 2-amino-3-cyano-6-(1H-indol-3-yl)-4-phenylpyridine derivatives were synthesized and their cytotoxic activity against A549, H460, HT-29 and SMMC-7721 cell lines was evaluated in vitro. Among them, ten compounds (10, 11, 14, 16, 17, 26, 27, 29, 30 and 31) displayed excellent anti-tumor activity against different cell lines. The most promising compound 27 showed strong anti-tumor activity against A549, H460, HT-29 and SMMC-7721 cell lines with IC50 values of 22, 0.23, 0.65 and 0.77 nM, which were 2.6-, 83-, 1.1 × 103- and 2.0 × 103- fold more active than MX-58151 (IC50 values of 0.058, 0.019, 0.70 and 1.53 μM), respectively.
- Zhang, Fan,Zhao, Yanfang,Sun, Li,Ding, Lu,Gu, Yucheng,Gong, Ping
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p. 3149 - 3157
(2011/06/26)
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- New 4-[(1-benzyl-1H-indol-3-yl)carbonyl]-3-hydroxyfuran-2(5H)-ones, β-diketo acid analogs as HIV-1 integrase inhibitors
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In addition to our recent report on a series of rationally designed benzylindolyldiketo acids acting as potent HIV-1 integrase strand transfer inhibitors, we disclose the results obtained with novel compounds chemically modified on the diketo acid moiety in order to investigate its influence on the biological activity and cytotoxicity. The activity of designed and synthesized 4-[(1-benzyl-1H-indol-3-yl)carbonyl]-3-hydroxyfuran-2(5H)-one derivatives lies in the micromolar range with regard to HIV IN enzymatic activity. The microwave-assisted synthesis was employed in some steps of the chemical procedures.
- Ferro, Stefania,Barreca, Maria Letizia,De Luca, Laura,Rao, Angela,Monforte, Anna Maria,Debyser, Zeger,Witvrouw, Myriam,Chimirri, Alba
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p. 292 - 298
(2008/02/10)
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- Towards the syntheses of N-H and N-alkylated derivatives of meridianins
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(Chemical Equation Presented) Novel N-H and N-alkylated derivatives of meridianins have been synthesized as potential antitumor agents by a two-step conversion of N-tosyl-3-acetylindoles or N-alkyl-3-acetylindoles to the corresponding enaminones using DMF-DMA, with or without added pyrrolidine. Further cyclization with guanidine gave the corresponding 2-aminopyrimidines. The structures of the compounds, thus obtained, were proved by 1H and 13C NMR spectroscopy, NOE experiments and X-ray analysis.
- Simon, Ga?lle,Couthon-Gourves, Hélène,Haelters, Jean-Pierre,Corbel, Bernard,Kervarec, Nelly,Michaud, Fran?ois,Meijer, Laurent
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p. 793 - 801
(2008/03/29)
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- Pharmacophore-based design of HIV-1 integrase strand-transfer inhibitors
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Using a training set of diketo-like acid HIV-1 integrase (IN) strand-transfer inhibitors, a 3D pharmacophore model was derived having quantitative predictive ability in terms of activity. The best statistical hypothesis consisted of four features (one hydrophobic aromatic region, two hydrogen-bond acceptors, and one hydrogen-bond donor) with r of 0.96. The resulting pharmacophore model guided the rational design of benzylindoles as new potent IN inhibitors, whose microwave-assisted synthesis and biological evaluation are reported.
- Barreca, Maria Letizia,Ferro, Stefania,Rao, Angela,De Luca, Laura,Zappalà, Maria,Monforte, Anna-Maria,Debyser, Zeger,Witvrouw, Myriam,Chimirri, Alba
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p. 7084 - 7088
(2007/10/03)
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- Structure activity of 3-Aryl-1,3-diketo-containing compounds as HIV-1 integrase inhibitors
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The 4-aryl-2-hydroxy-4-oxo-2-butenoic acids and their isosteric tetrazoles are among an emerging class of aryl β-diketo (ADK)-based agents which exhibit potent inhibition of HIV-1 integrase (IN)-catalyzed strand transfer (ST) processes, while having much
- Pais, Godwin C. G.,Zhang, Xuechun,Marchand, Christophe,Neamati, Nouri,Cowansage, Kiriana,Svarovskaia, Evguenia S.,Pathak, Vinay K.,Tang, Yun,Nicklaus, Marc,Pommier, Yves,Burke Jr., Terrence R.
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p. 3184 - 3194
(2007/10/03)
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