- Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate
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Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.
- Li, Yudong,Li, Yuehui,Luo, Shuping,Wang, Menglan,Wu, Qing-An
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supporting information
p. 3085 - 3090
(2019/08/07)
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- Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives
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A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[b]naphthalene derivatives in moderate to excellent yields under mild conditions.
- Li, Peng-Hua,Yu, Liu-Zhu,Zhang, Xiao-Yu,Shi, Min
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p. 4516 - 4520
(2018/08/09)
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- Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles
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A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L-1 and 0.09 μmol L-1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L-1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target. This journal is
- Chen, Jiuxi,Ye, Leping,Su, Weike
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supporting information
p. 8204 - 8211
(2015/01/08)
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- Synthesis of 2-aminobenzophenone derivatives and their anticancer activity
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A number of 2-aminobenzophenones have been synthesized by acylation of para-chloroaniline with different 2-, 3-, 4-chloro-or fluorobenzoyl chloride in solid state via the Friedel-Crafts reaction. Synthesized compounds were characterized by 1H and 13C NMR, Fourier transform-infrared, ultraviolet-visible spectroscopy, mass spectrometry, and elemental analysis. Evaluation of biological activity in vitro showed that the selected compounds 9, 10, and 13 have potential anticancer activity. The presence of one chlorine atom in the second aromatic ring of the benzophenone molecule makes it more active.
- Cortez-Maya,Cortes Cortes,Hernandez-Ortega,Apan, T. Ramirez,Martinez-Garcia
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experimental part
p. 46 - 54
(2011/10/31)
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- Synthesis of quinolin-2-one alkaloid derivatives and their inhibitory activities against HIV-1 reverse transcriptase
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Based on an established common pharmacophore of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNTTIs), a series of quinolin-2-one derivatives were synthesized and assayed for their in vitro activities against HIV-1 reverse transcriptase (RT) for the first time. Some of the tested compounds were active against HIV-1 RT. Compounds 4a2 and 4d2 showed inhibitory activities with IC50 values of 0.21 and 0.15 μM, respectively, with a mode of interaction with RT residues of the allosteric pocket similar to that of efavirenz.
- Cheng, Pi,Gu, Qiong,Liu, Wei,Zou, Jian-Feng,Ou, Yang-Yong,Luo, Zhong-Yong,Zeng, Jian-Guo
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p. 7649 - 7661
(2011/11/05)
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- An enantiopure galactose oxidase model: synthesis of chiral amino alcohols through oxidative kinetic resolution catalyzed by a chiral copper complex
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An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)-BINAM and Cu(OTf)2, and the enantiopure GO model has been effectively used in situ as an efficient chiral catalyst for the synthesis of chiral amino alcohols through oxidative kinetic resolution (OKR), where molecular oxygen is used as the sole oxidant. Under the proposed catalytic conditions, both ortho- and para-substituted amino alcohols were resolved with good to excellent enantiomeric excesses through oxidative kinetic resolution.
- Mannam, Sreedevi,Sekar, Govindasamy
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experimental part
p. 497 - 502
(2009/07/18)
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- Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives
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A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively).
- Cheng, Pi,Zhang, Quan,Ma, Yun-Bao,Jiang, Zhi-Yong,Zhang, Xue-Mei,Zhang, Feng-Xue,Chen, Ji-Jun
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supporting information; experimental part
p. 3787 - 3789
(2009/04/06)
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- Synthesis and spectral properties of 2-[(o- and p-substituted)aminophenyl]-3H-5-[(o- and p-substituted)phenyl]-7-chloro-1,4-benzodiazepines
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A series of twelve new 2-[(o- and p-substituted)aminophenyl]-3H-5-[(o- and p-substituted)phenyl]-7-chloro-1,4-benzodiazepines, which have possible pharmacological properties has been obtained. The synthesis was carried out following six steps. The structure of all products was corroborated by ir, 1H nmr, 13C nmr and ms. In addition for the compound 2-(o-chloroaminophenyl)-3H-5-(o-fluorophenyl)-7-chloro-1,4-benzodiazepine 7, its structure was confirmed by X-ray diffraction.
- Cortes Cortes,Salazar Franco,Garcia Mellado
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p. 663 - 669
(2007/10/03)
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- Screening, detection and biotransformation of lormetazepam, a new hypnotic agent from the 1,4-benzodiazepine series
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The paper describes a screening procedure for 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1H-1,4-benzodiaze pin-2-one (lormetazepam, Noctamid) and other important analytical data (TLC, GLC, UV-, IR- and mass spectra) of this new benzodiazepine derivative. Screening results after a single p.o. dose of 1 mg lormetazepam (Noctamid-1) are also reported.
- Schutz,Fitz
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p. 177 - 183
(2007/10/02)
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- Benzodiazepine derivatives and pharmaceutical compositions containing said derivatives
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Novel 4H-pyrrolo[1,2-a][1,4]benzodiazepine derivatives of the formula STR1 wherein at least one of R1, R2 and R3 represent lower alkyl and the remainder hydrogen, R4 represents hydrogen or lower alkyl, ring A optionally contains at least one substituent selected from halogen, nitro and trifluoromethyl, and ring B optionally contains at least one substituent selected from halogen, nitro, trifluoromethyl, lower alkyl and lower alkoxy; and novel intermediates thereof expressed by the formula STR2 wherein Z represents protected amino. Compounds of formula (I) are prepared by subjecting compounds of formula (II) to protective group-elimination and cyclization. The compounds of formula (I) and acid addition salts thereof have useful anti-anxietic, sedative, anti-convulsant, muscle relaxant and hypnotic, and their toxicity is low.
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