3055-86-5Relevant articles and documents
Benzyne-Mediated Nonconcerted Pathway toward Synthesis of Sterically Crowded [5]- and [7]Oxahelicenoids, Stereochemical and Theoretical Studies, and Optical Resolution of Helicenoids
Gawade, Prashant M.,Khose, Vaibhav N.,Badani, Purav M.,Hasan, Mohammed,Kaabel, Sandra,Mobin, Shaikh M.,Borovkov, Victor,Karnik, Anil V.
, (2019)
Synthesis of [5]- and [7]oxahelicenoids via Diels-Alder reaction of sterically crowded bichromenes with benzyne is presented. Studies carried out on Diels-Alder addition product establish the unusual preference for a stepwise mechanism over the concerted reaction pathway. This high yielding general synthetic protocol affords unexpected anti cycloadducts [5]- and [7]oxahelicenoids, as confirmed by crystallographic analysis. To rationalize these intriguing antiaddition products, the reaction mechanism was elucidated by means of DFT analysis. Additionally, hydroxy-functionalized [7]oxahelicenoid has been resolved in its optically pure forms.
Design, synthesis and preliminary bioactivity evaluation of bitopic benzopyranomorpholine analogues as selective dopamine D3 receptor ligands as anti-drug addiction therapeutic agents
Cai, Jin,Chen, Xixi,Huang, Mingqi,Ji, Min,Wang, Yuhong
, (2021/08/09)
Three series of bitopic benzopyranomorpholine analogues were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine D3 receptor. Binding affinities of target compounds were determined using the method of radioligand binding assay. Most compounds demonstrated considerable binding affinities and selectivity for D3 receptor. Besides, the compounds were screened for their ability to alleviate withdrawal symptoms of opioid addiction in animal behavioral models. The results showed that compound 20h displayed nanomolar affinity for the D3R, and exhibited anti-drug addiction efficacy in the animal model of of naloxone-induced withdrawal symptoms in morphine-dependent mice.
Benzyne-Mediated Nonconcerted Pathway toward Synthesis of Sterically Crowded [5]- And [7]Oxahelicenoids, Stereochemical and Theoretical Studies, and Optical Resolution of Helicenoids
Badani, Purav M.,Borovkov, Victor,Gawade, Prashant M.,Hasan, Mohammed,Kaabel, Sandra,Karnik, Anil V.,Khose, Vaibhav N.,Mobin, Shaikh M.
, p. 860 - 868 (2021/08/24)
Synthesis of [5]- and [7]oxahelicenoids via Diels-Alder reaction of sterically crowded bichromenes with benzyne is presented. Studies carried out on Diels-Alder addition product establish the unusual preference for a stepwise mechanism over the concerted reaction pathway. This high yielding general synthetic protocol affords unexpected anti cycloadducts [5]- and [7]oxahelicenoids, as confirmed by crystallographic analysis. To rationalize these intriguing antiaddition products, the reaction mechanism was elucidated by means of DFT analysis. Additionally, hydroxy-functionalized [7]oxahelicenoid has been resolved in its optically pure forms.
