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An eco-friendly catalytic system for multicomponent, one-pot synthesis of novel spiro-chromeno indoline-triones and their anti-prostate cancer potentials evaluated via alkaline phosphatase inhibition mechanism
Bioorganic Chemistry ( IF 5.1 ) Pub Date : 2018-08-06 , DOI: 10.1016/j.bioorg.2018.07.037
M. Rajesh Kumar , A. Manikandan , A. Sivakumar , V. Violet Dhayabaran

A green and efficient straightforward tactic for the one-pot regioselective synthesis of novel 10,10-dimethyl-9,10,11,11a-tetrahydro-6H-spiro[chromeno[4,3–b]chromene-7,3′-indoline]-2′,6,8 (7aH) -triones (4a-n) in one-pot modus has been established using eco-friendly p-toluenesulphonic acid as catalyst. Among the solvents that were used for synthesis, 4a-n were suitably synthesized with maximum yield (90–98%) in water. We avoided column purification and the formed by-product in the process is environmental-friendly. Hence, this reaction may consider as an astonishing piece work in this study, why because, the reaction mechanism that depends on the nature of the group attached to the isatin ring nitrogen atom. The main advantage of this protocol includes short reaction time, good yield, easy to work-up, practical simplicity, high regioselectivity and reduced pollutant, cost and avoids tedious purification. These pharmaceutically important compounds (4a-n) were recognized for their alkaline phosphatase inhibition and prostate cancer medication capabilities. The selective activity relation between alkaline phosphatase and prostate cancer was unveiled through the interaction of 4a-n to Human alkaline phosphatase (PDB ID: 1EW2).



中文翻译:

通过碱性磷酸酶抑制机制评估新型螺-铬基二氢吲哚三酮的多组分一锅合成及其抗前列腺癌潜力的生态友好催化体系

一种绿色高效的简单策略,用于一锅区域选择性合成新型10,10-二甲基-9,10,11,11a-四氢-6H-螺[chromeno [4,3-b] chromene-7,3'-以环保型甲苯磺酸为催化剂,建立了一锅法的二氢吲哚] -2′,6,8(7​​aH)-三酮(4a-n)。在用于合成的溶剂中,4a-n在水中以最大产率(90–98%)适当合成。我们避免了色谱柱纯化,并且在此过程中形成的副产物对环境友好。因此,该反应在本研究中可能被认为是一项惊人的工作,为什么呢,因为该反应机理取决于与环素氮原子相连的基团的性质。该方案的主要优点包括反应时间短,收率高,易于后处理,操作简便,区域选择性高,污染物少,成本高以及避免繁琐的纯化。这些药学上重要的化合物(4a-n)因其碱性磷酸酶抑制作用和前列腺癌的药物治疗能力而被公认。通过4a-n与人碱性磷酸酶(PDB ID:1EW2)的相互作用揭示了碱性磷酸酶与前列腺癌之间的选择性活性关系。

更新日期:2018-08-06
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