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Probes for Narcotic Receptor Mediated Phenomena. 37. Synthesis and Opioid Binding Affinity of the Final Pair of Oxide-Bridged Phenylmorphans the ortho- and para-b Isomers and Their N-Phenethyl Analogues and the Synthesis of the N-Phenethyl Analogues of the ortho- and para-d Isomers

机译：麻醉受体介导现象的探针。 37.氧化物桥连的苯吗啡酮邻-和对-b异构体及其N-苯乙基类似物的最终对的合成和阿片类药物的亲和力以及邻-和对-d异构体的N-苯乙基类似物的合成

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In the isomeric series of 12 racemic topologically rigid N-methyl analogues of oxide-bridged phenylmorphans, all but two of the racemates, the ortho- and para-b-oxide-bridged phenylmorphans >20 and >12, have remained to be synthesized. The b-isomers were very difficult to synthesize because of the highly strained 5,6-trans-fused ring junction that had to be formed. Our successful strategy required functionalization of the position para (or ortho) to a fluorine atom on the aromatic ring using an electron-withdrawing nitro group to activate that fluorine. The racemic N-phenethyl analogues >24 and >16 were moderately potent κ-receptor antagonists in the [³⁵S]GTPγS assay. We synthesized the N-phenethyl-substituted oxide-bridged phenylmorphans in the ortho- and para-d oxide-bridged phenylmorphan series (>51 and >52) which had not been previously evaluated using contemporary receptor binding assays to see whether they also have higher affinity for opioid receptors than their N-methyl relatives >46 and >47.

机译：在氧化桥联苯吗啡的12个外消旋拓扑刚性N-甲基类似物的异构体系列中，除两个外消旋物外，所有邻消旋体都是邻-和顺-b-氧化物桥联的苯吗啡^{> 20 < / strong>和> 12 ，还有待综合。由于必须形成高度应变的5,6-反式-稠合的环结，因此很难合成b-异构体。我们成功的策略需要使用吸电子硝基将芳族环上的对位（或邻位）官能化为氟原子。在[^{35 S]GTPγS分析中，外消旋的N-苯乙基类似物> 24 和> 16 是中等有效的κ受体拮抗剂。我们合成了邻位和对位氧化物桥连的苯吗啡^{系列（> 51 和> 52 ）（之前尚未使用当代受体结合测定法进行评估），以查看它们是否对阿片样物质受体也比其N-甲基亲戚> 46 和> 47 具有更高的亲和力。}}}

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期刊名称 other
作者
Muneaki Kurimura; Hehua Liu; Agnieszka Sulima; Akihiro Hashimoto; Anna K. Przybyl; Etsuo Ohshima; Shinichi Kodato; Jeffrey R. Deschamps; Christina M. Dersch; Richard B. Rothman; Yong Sok Lee; Arthur E. Jacobson; Kenner C. Rice;
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年(卷),期 -1(51),24
年度 -1
页码 7866–7881
总页数 37
原文格式 PDF
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Oxide-bridged 5-phenylmorphans N-methyl and N-phenethyl-substituted ortho- and para-b-isomers N-methyl and N-phenethyl-substituted ortho- and para-d-isomers opioid receptor binding functional assay;

机译：氧化物桥联的5-苯基吗啉;N-甲基和N-苯乙基取代的邻和对b异构体;N-甲基和N-苯乙基取代的邻和对d异构体;阿片受体结合;功能测定;

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1. Probes for Narcotic Receptor Mediated Phenomena. 37.(1) Synthesis and Opioid Binding Affinity of the Final Pair of Oxide-Bridged Phenylmorphans, the Ortho- and Para-b-Isomers and Their N-Phenethyl Analogues, and the Synthesis of the N-Phenethyl Analo [J] . Kurimura M, Liu H, Sulima A, Journal of Medicinal Chemistry . 2008,第24期

机译：麻醉受体介导现象的探针。 37.（1）氧化物桥联苯吗啡，邻-对-对-对-异构体及其N-苯乙基类似物的最终对的合成和阿片类药物的亲和力以及N-苯乙基类似物的合成
2. Probes for narcotic receptor mediated phenomena. Part 42: synthesis and in vitro pharmacological characterization of the N-methyl and N-phenethyl analogues of the racemic ortho-c and para-c oxide-bridged phenylmorphans. [J] . Kim JH, Deschamps JR, Rothman RB, Bioorganic and medicinal chemistry . 2011,第11期

机译：麻醉受体介导现象的探针。第42部分：外消旋邻-c和对-c氧化物桥接的苯基吗啡烷的N-甲基和N-苯乙基类似物的合成和体外药理学表征。
3. Probes for narcotic receptor mediated phenomena. Part 42: synthesis and in vitro pharmacological characterization of the N-methyl and N-phenethyl analogues of the racemic ortho-c and para-c oxide-bridged phenylmorphans. [J] . Kim JH, Deschamps JR, Rothman RB, Bioorganic and medicinal chemistry . 2011,第11期

机译：麻醉受体介导现象的探针。第42部分：外消旋邻-c和对-c氧化物桥接的苯基吗啡烷的N-甲基和N-苯乙基类似物的合成和体外药理学表征。
4. Synthesis of 2,3,4,4A,9,10-hexahydro-7-methoxy-4A-methylphenanthren-2-one by aryl radical cyclization. Studies directed toward the asymmetric total synthesis of (+)-cepharamine. Asymmetric and racemic syntheses, opioid receptor affinities, and antinociceptive effects of a new class of structural analogues of the morphine alkaloids. [D] . Wang, Aihua. 1997

机译：通过芳基环化反应合成2,3,4,4A，9,10-六氢-7-甲氧基-4A-甲基菲-2-研究针对（+）-头孢拉明的不对称全合成。非对称和外消旋的合成，阿片受体的亲和力以及吗啡生物碱的新型结构类似物的镇痛作用。
5. Probes for narcotic receptor mediated phenomena. 42. Synthesis and in vitro pharmacological characterization of the N-methyl and N-phenethyl analogues of the racemic ortho-c and para-c oxide-bridged phenylmorphans [O] . Jin-Hee Kim, Jeffrey R. Deschamps, Richard B. Rothman, -1

机译：麻醉受体介导现象的探针。 42.外消旋ORTHO-C和氧化丙纤维苯甲酯的N-甲基和N-苯乙烯类似物的合成和体外药理学表征
6. Probes for Narcotic Receptor Mediated Phenomena. 37. Synthesis and Opioid Binding Affinity of the Final Pair of Oxide-Bridged Phenylmorphans, the Ortho- and Para-b-Isomers and Their N-Phenethyl Analogues, and the Synthesis of the N-Phenethyl Analogues of the Ortho- and Para-d-Isomers [O] . Muneaki Kurimura, Hehua Liu, Agnieszka Sulima, 2009

机译：麻醉受体介导现象的探针。 37.最后一对氧化物桥面苯二甲苯甲酯，邻和对等异构体及其N-苯甲基类似物的合成和阿片类药物结合亲和力，以及邻晶和律师的N-苯乙基类似物的合成 - 异常
7. Vitamin D3 Analogues with Low Vitamin D Receptor Binding Affinity RegulateChondrocyte Proliferation, Proteoglycan Synthesis, and Protein Kinase C Activity [R] . Greising, D. M. 1997

机译：具有低维生素D受体结合亲和力的维生素D3类似物调节软骨细胞增殖，蛋白多糖合成和蛋白激酶C活性

Probes for Narcotic Receptor Mediated Phenomena. 37. Synthesis and Opioid Binding Affinity of the Final Pair of Oxide-Bridged Phenylmorphans the ortho- and para-b Isomers and Their N-Phenethyl Analogues and the Synthesis of the N-Phenethyl Analogues of the ortho- and para-d Isomers

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