128076-64-2Relevant academic research and scientific papers
Synergistic Cooperative Effect of Sodium borohydride-Iodine Towards Cascade C?N and C?S/Se Bond Formation: One-pot Regioselective Synthesis of 3-Sulfenyl/selenyl Indoles and Mechanistic Insight
Lavekar, Aditya G.,Equbal, Danish,Saima,Sinha, Arun K.
supporting information, p. 180 - 185 (2018/01/12)
In this work, a new strategy to synthesize 3-sulfenyl/selenyl indole is reported wherein LC?MS reveals a novel insight into synergistic cooperative effect of NaBH4-I2 which allows cascade C?N and C?S/C?Se bond formations via reduction-nucleophilic cyclization-chalcogenylation, three steps in one-pot, towards regioselective synthesis of diverse 3-chalcogenyl indoles including 5-bromo-3-[(3,4,5-trimethoxyphenyl)thio]-1H-indole, a known lead anticancer compound, directly from 2-amino-phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition-metal-free condition. (Figure presented.).
New homocamptothecins: Synthesis, antitumor activity, and molecular modeling
Miao, Zhenyuan,Sheng, Chunquan,Zhang, Wannian,Ji, Haitao,Zhang, Jing,Shao, Luecheng,You, Liang,Zhang, Min,Yao, Jianzhong,Che, Xiaoyin
, p. 1493 - 1510 (2008/09/17)
Homocamptothecins (hCPTs) represent a class of new emerging antitumor agents, which contains a seven-membered β-hydroxylactone in place of the conventional six-membered α-hydroxylactone ring (E ring) of camptothecins. Some novel 7-substituted hCPTs were designed and synthesized based on a newly developed synthetic route which couples ring A with ring C, E and D. Most of the synthesized compounds exhibit very high cytotoxic activity on tumor cell line A549. Some compounds, such as 9b, 9l, and 9y, show broad in vitro antitumor spectrum and are more potent than topotecan. Three-dimensional quantitative structure-activity relationship (3D-QSAR) methods, CoMFA and CoMSIA, were applied to explain the structure-activity relationship (SAR) of the synthesized compounds. Furthermore, molecular docking was used to clarify the binding mode of the synthesized compounds to human DNA topoisomerase I. The important hydrophobic, base-pair stacking, and hydrogen-bonding interactions were observed between the hCPT derivatives and their receptor. The results from molecular modeling will guide the design of novel hCPTs with higher antitumor activity.
Derivatives of kynurenine as inhibitors of rat brain kynurenine aminotransferase
Varasi,Della Torre,Heidempergher,Pevarello,Speciale,Guidetti,Wells,Schwarcz
, p. 11 - 21 (2007/10/03)
The structural requirements of the catalytic site of kynurenine aminotransferase (KAT), the enzyme responsible for the conversion of L-kynurenine (KYN) to kynurenic acid (KYNA), were examined using analogs and derivatives of KYN. KYNA production from KYN was monitored in rat brain homogenates and brain tissue slices. Modification of KYN's acylalanine side chain or its ring amino group resulted in compounds which did not substantially affect KYNA synthesis. Ring chlorination in positions 3, 4, 5 and 6 yielded KYN analogs which interfered with KYNA production. L-5-Cl-KYN was the most active of the chlorinated kynurenines, and one of the most potent of several other 5-substituted kynurenines. L-5-Cl-KYN was an excellent substrate of KAT, yielding 6-Cl-KYNA. Finally, in kinetic studies, L-5-Cl-KYN (K(i) = 5.4 μM) was found to have an approximately five times higher affinity to the enzyme than the natural substrate KYN (K(m) = 28 μM).
Substituted kynurenines and process for their preparation
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, (2008/06/13)
The present invention relates to the use in the treatment of cognitive disorders associated with the aging processes of the brain and perinatal brain disorders of compounds which act as inhibitors of the enzyme kynurenine aminotransferase (KAT). The prese
