103069-52-9Relevant academic research and scientific papers
An indium-promoted alternative to the knoevenagel condensation of aldehydes with methyl acetoacetate
Paquette, Leo A.,Kern, Benjamen E.,Mendez-Andino, Jose
, p. 4129 - 4132 (1999)
Addition of methyl (E)-4-bromo-3-methoxycrotonate to aldehydes in the presence of indium and water delivers β-hydroxy esters, acidic hydrolysis of which leads to Knoevenagel-like adducts.
Intermolecular Reductive Couplings of Arylidene Malonates via Lewis Acid/Photoredox Cooperative Catalysis
McDonald, Benjamin R.,Scheidt, Karl A.
supporting information, p. 6877 - 6881 (2018/11/02)
A cooperative Lewis acid/photocatalytic reduction of arylidene malonates yields a versatile radical anion species. This intermediate preferentially undergoes intermolecular radical-radical coupling reactions, and not the conjugate addition-dimerization reactivity typically observed in the single-electron reduction of conjugate acceptors. Reported here is the development of this open-shell species in intermolecular radical-radical cross couplings, radical dimerizations, and transfer hydrogenations. This reactivity underscores the enabling modularity of cooperative catalysis and demonstrates the utility of stabilized enoate-derived radical anions in intermolecular bond forming reactions.
Design and synthesis of orally bioavailable 4-methyl heteroaryldihydropyrimidine based hepatitis B virus (HBV) capsid inhibitors
Qiu, Zongxing,Lin, Xianfeng,Zhou, Mingwei,Liu, Yongfu,Zhu, Wei,Chen, Wenming,Zhang, Weixing,Guo, Lei,Liu, Haixia,Wu, Guolong,Huang, Mengwei,Jiang, Min,Xu, Zhiheng,Zhou, Zheng,Qin, Ning,Ren, Shuang,Qiu, Hongxia,Zhong, Sheng,Zhang, Yuxia,Zhang, Yi,Wu, Xiaoyue,Shi, Liping,Shen, Fang,Mao, Yi,Zhou, Xue,Yang, Wengang,Wu, Jim Z.,Yang, Guang,Mayweg, Alexander V.,Shen, Hong C.,Tang, Guozhi
, p. 7651 - 7666 (2016/09/04)
Targeting the capsid protein of hepatitis B virus (HBV) and thus interrupting normal capsid formation have been an attractive approach to block the replication of HBV viruses. We carried out multidimensional structural optimizations based on the heteroaryldihydropyrimidine (HAP) analogue Bay41-4109 (1) and identified a novel series of HBV capsid inhibitors that demonstrated promising cellular selectivity indexes, metabolic stabilities, and in vitro safety profiles. Herein we disclose the design, synthesis, structureactivity relationship (SAR), cocrystal structure in complex with HBV capsid proteins and in vivo pharmacological study of the 4-methyl HAP analogues. In particular, the (2S,4S)-4,4-difluoroproline substituted analogue 34a demonstrated high oral bioavailability and liver exposure and achieved over 2 log viral load reduction in a hydrodynamic injected (HDI) HBV mouse model.
Synthesis and application of ionic liquid phase-supported β-aminocrotonate for access to asymmetric 1,4- dihydropyridines
Bazureau, Jean Pierre,Legeay, Jean-Christophe,Carrie, Daniel,Paquin, Ludovic,Jacques, Jean,Eynde, Vanen
experimental part, p. 91 - 96 (2010/06/19)
Ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-l,4-dihydropyridine-3, 5dicarboxylate or nitrendipine was prepared in four steps with high overall yield from ionic liquid phase bound b-aminocrotonate. The asymmetric 1,4-dihydropyridine scaffolds were built using a sequential approach according to ionic liquid-phase organic synthesis (IoLiPOS) methodology.
Design and synthesis of novel α(1a) adrenoceptor-selective antagonists. 1. Structure-activity relationship in dihydropyrimidinones
Nagarathnam, Dhanapalan,Miao, Shou Wu,Lagu, Bharat,Chiu, George,Fang, James,Dhar, T. G. Murali,Zhang, Jack,Tyagarajan, Sriram,Marzabadi, Mohammad R.,Zhang, Fengqi,Wong, Wai C.,Sun, Wanying,Tian, Dake,Wetzel, John M.,Forray, Carlos,Chang, Raymond S. L.,Broten, Theodore P.,Ransom, Richard W.,Schorn, Terry W.,Chen, Tsing B.,O'Malley, Stacey,Kling, Paul,Schneck, Kathryn,Bendesky, Robert,Harrell, Charles M.,Vyas, Kamlesh P.,Gluchowski, Charles
, p. 4764 - 4777 (2007/10/03)
Dihydropyrimidinones such as compound 12 exhibited high binding affinity and subtype selectivity for the cloned human α(1a) receptor. Systematic modifications of 12 led to identification of highly potent and subtype- selective compounds such as (+)-30 and
Crystal Structures and Pharmacologic Activities of 1,4-Dihydropyridine Calcium Channel Antagonists of the Isobutyl Methyl 2,6-Dimethyl-4-(substituted phenyl)-1,4-dihydropyridine-3,5-dicarboxylate (Nisoldipine) Series
Fossheim, R.,Joslyn, A.,Solo, A. J.,Luchowski, E.,Rutledge, A.,Triggle, D. J.
, p. 301 - 305 (2007/10/02)
A series of isobutyl methyl 2,6-dimethyl-4-(X-substituted phenyl)-1,4-dihydropyridine-3,5-dicarboxylates (X= H, 2-NO2, 3-NO2, 3-CN, 3-MeO, 4-F, 2-CF3, 3-CF3, and 4-Cl) related to and including nisoldipine (X= 2-NO2) has been synthesized, their solid-state
