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Antimony salt-promoted cyclization facilitating on-DNA syntheses of dihydroquinazolinone derivatives and its applications

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中国化学快报:英文版 2023年第8期34卷 201-207页

作者： Qigui Nie Jie Sun Xianfu Fang Xun He Feng Xiong Gong Zhang Yangfeng Li Yizhou Li Chongqing Key Laboratory of Natural Product Synthesis and Drug Research Innovative Drug Research CenterSchool of Pharmaceutical SciencesChongqing UniversityChongqing 401331China Shenzhen Innovation Center for Small Molecule Drug Discovery Co. Ltd.Shenzhen 518110China Chemical Biology Research Center School of Pharmaceutical SciencesChongqing UniversityChongqing 401331China Key Laboratory of Biorheological Science and Technology Ministry of EducationCollege of BioengineeringChongqing UniversityChongqing 400044China Beijing National Laboratory for Molecular Sciences Beijing 100190China

DNA-encoded chemical libraries technology has become a novel approach to finding hit compounds in early drug *** chemical space in a DEL would be expanded to realize its full potential,especially when integrating privileged scaffold dihydroquinazoline that has demonstrated a variety of diverse *** by the requirement of parallel combinatorial synthesis,we here report a facile synthesis of on-DNA dihydroquinazolinone from aldehyde and *** DNA-compatible reaction was promoted by antimony trichloride,which has been proven to accelerate the reaction and improve ***,the broad substrate scope of aldehydes and anthranilamides was explored under the mild reaction condition to achieve moderate-to-excellent conversion *** further applied the reaction into on-DNA macrocyclization,obtaining macrocycles embedded dihydroquinazolinone scaffold in synthetically useful conversion yields.

关键词： DNA-encoded chemical libraries Antimony dihydroquinazolinone Macrocyclization DNA-compatible chemistry

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Electrochemical utilization of methanol and methanol-d4 as a C1 source to access(deuterated) 2,3-dihydroquinazolin-4(1H)-one

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Chinese Chemical Letters 2022年第3期33卷 1559-1562页

作者： Mingzhu Liu Liang Xu Yu Wei School of Chemistry and Chemical Engineering Key Laboratory for Green Processing of Chemical Engineering of Xinjiang BingtuanShihezi UniversityShihezi 832003China

Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with *** cyclization reaction proceeds conveniently(room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.

关键词： Electrochemistry Heterocycles dihydroquinazolinone Aminobenzamide C1 source

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Enantioselective Enynylation of Cyclic N-Acyl Ketimines:Access to Chiral Trifluoromethylated Tertiary Carbinamines

Enantioselective Enynylation of Cyclic N-Acyl Ketimines:Acce...

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中国化学会全国第十一届有机合成化学学术研讨会

作者： Fa-Guang Zhang Shen Li Jing Nie Jun-An Ma Department of Chemistry Tianjin University

Trifluoromethyl-substituted dihydroquinazolinones are important structural motifs found in many pharmaceuticals and bioactive ***,among these compounds,DPC-961,DPC-963,DPC-082,and DPC-083 are nonnucleoside reverse transcriptase inhibitors(NNRTIs)that show promise for the treatment of HIV as well as new mutant strains of the virus. As a result of their important usefulness,developing new,highly enantioselective methods for the construction of these compounds and analogues has become the subject of intensive research in the fields of synthetic and medicinal *** from these anti-HIV drugs,my research group developed a new enantioselective enynylation reaction by using trifluoromethyl-substituted dihydroquinazolinones as electrophilic *** synthetic transformation gave rise to the analogues of the anti-HIV drugs DPC-961 and DPC-083(Figure 1). It is likely that the compounds prepared here will provide novel therapeutic agents and useful biological tools.

关键词： Enantioselectivity Enynylation dihydroquinazolinone Synthesis

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