Department of Chemistry, Bishop Heber College, Tiruchirappalli, India.
Department of Biotechnology, School of Bio-Sciences and Technology, VIT University, Vellore 632014, India.
Bioorg Chem. 2018 Dec;81:44-54. doi: 10.1016/j.bioorg.2018.07.037. Epub 2018 Aug 6.
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).
一种绿色、高效、直接的一锅法区域选择性合成新型 10,10-二甲基-9,10,11,11a-四氢-6H-螺[色烯[4,3-b]色烯-7,3'-吲哚啉]-2',6,8(7aH)-三酮(4a-n)的方法已经建立，使用环保的对甲苯磺酸作为催化剂。在所使用的溶剂中，4a-n 以最高产率(90-98%)在水中适当地合成。我们避免了柱纯化，并且过程中形成的副产物是环保的。因此，该反应可以被认为是本研究中的一项惊人的工作，原因是，反应机制取决于与靛基质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、产率高、易于处理、实用简单、高区域选择性和减少污染物、成本，并避免繁琐的纯化。这些具有重要药用价值的化合物(4a-n)因其对碱性磷酸酶的抑制作用和前列腺癌治疗作用而得到认可。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。
