6-(tributylstannanyl)-6-(2,3-dihydro-3,7-dimethyl-2-oxobenzoxazol-5-yl)hex-5-enoic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 6-(tributylstannanyl)-6-(2,3-dihydro-3,7-dimethyl-2-oxobenzoxazol-5-yl)hex-5-enoic acid methyl ester
• 英文别名: 6-(3,7-Dimethyl-2-oxo-2,3-dihydro-benzoxazol-5-yl)-6-(tributylstannanyl)-hex-5-enoic Acid Methyl Ester；methyl 6-(3,7-dimethyl-2-oxo-1,3-benzoxazol-5-yl)-6-tributylstannylhex-5-enoate
• 化学式: C₂₈H₄₅NO₄Sn
• 分子量: 578.38
• InChiKey: FXQKLPDPSZHENJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.55
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(tributylstannanyl)-6-(2,3-dihydro-3,7-dimethyl-2-oxobenzoxazol-5-yl)hex-5-enoic acid methyl ester 、 间溴苯甲腈 在 二(三叔丁基膦)钯 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 65.0h， 以3%的产率得到methyl (Z)-6-(3-cyanophenyl)-6-(3,7-dimethyl-2-oxo-1,3-benzoxazol-5-yl)hex-5-enoate
  参考文献：
  名称：

  Replacement of the Metabolically Labile Methyl Esters in the Alkenyldiarylmethane Series of Non-Nucleoside Reverse Transcriptase Inhibitors with Isoxazolone, Isoxazole, Oxazolone, or Cyano Substituents

  摘要：

  The alkenyldiarylmethanes (ADAMs) are a unique class of non-nucleoside reverse transcriptase inhibitors that have potential value in the treatment of HIV/AIDS. However, the potential usefulness of the ADAMs is limited by the presence of metabolically labile methyl ester moieties. A series of novel ADAMs were therefore designed and synthesized in order to replace the metabolically labile methyl ester moieties of the existing ADAM lead compounds with hydrolytically stable, fused isoxazolone, isoxazole, oxazolone, or cyano substituents on the aromatic rings. The methyl ester and methoxy substituents on both of the aromatic rings in the parent compound 1 were successfully replaced with metabolically stable moieties with retention of anti-HIV activity and a general decrease in cytotoxicity.

  DOI：

  10.1021/jm060449o
• 作为产物：
  描述：

  6-(3,7-dimethyl-2-oxo-2,3-dihydrobenzoxazol-5-yl)hex-5-ynoic acid methyl ester 、 三正丁基氢锡 在 四(三苯基膦)钯 氩 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 反应 6.83h， 以to afford the vinylstannane 72 (3.07 g) as oil in 90% yield的产率得到6-(tributylstannanyl)-6-(2,3-dihydro-3,7-dimethyl-2-oxobenzoxazol-5-yl)hex-5-enoic acid methyl ester
  参考文献：
  名称：

  Alkenyldiarylmethanes, Fused Analogs And Syntheses Thereof

  摘要：

  本文介绍了一种非核苷类的HIV-1反转录酶抑制剂。这些抑制剂可以作为治疗HIV感染的联合疗法的一部分使用。所述化合物具有抗病毒效力。此外，所述化合物具有代谢稳定性。本文还描述了制备非核苷类HIV-1反转录酶抑制剂的过程。

  公开号：

  US20080300288A1

文献信息

• Alkenyldiarylmethanes, Fused Analogs And Syntheses Thereof
  申请人：Cushman Mark S.

  公开号：US20080300288A1

  公开（公告）日：2008-12-04

  Non-nucleoside inhibitors of HIV-1 reverse transcriptase are described. Such inhibitors may be used as part of a combination therapy to treat HIV infection. Compounds described herein exhibit antiviral potency. In addition, compounds described herein exhibit metabolic stability. Also described herein are processes for preparing Non-nucleoside inhibitors of HIV-1 reverse transcriptase.

  HIV-1反转录酶的非核苷类抑制剂被描述。这些抑制剂可以作为治疗HIV感染的联合疗法的一部分使用。本文描述的化合物具有抗病毒效力。此外，本文描述的化合物具有代谢稳定性。本文还描述了制备HIV-1反转录酶非核苷类抑制剂的过程。
• Replacement of the Metabolically Labile Methyl Esters in the Alkenyldiarylmethane Series of Non-Nucleoside Reverse Transcriptase Inhibitors with Isoxazolone, Isoxazole, Oxazolone, or Cyano Substituents
  作者：Bo-Liang Deng、Tracy L. Hartman、Robert W. Buckheit,、Christophe Pannecouque、Erik De Clercq、Mark Cushman

  DOI：10.1021/jm060449o

  日期：2006.8.1

  The alkenyldiarylmethanes (ADAMs) are a unique class of non-nucleoside reverse transcriptase inhibitors that have potential value in the treatment of HIV/AIDS. However, the potential usefulness of the ADAMs is limited by the presence of metabolically labile methyl ester moieties. A series of novel ADAMs were therefore designed and synthesized in order to replace the metabolically labile methyl ester moieties of the existing ADAM lead compounds with hydrolytically stable, fused isoxazolone, isoxazole, oxazolone, or cyano substituents on the aromatic rings. The methyl ester and methoxy substituents on both of the aromatic rings in the parent compound 1 were successfully replaced with metabolically stable moieties with retention of anti-HIV activity and a general decrease in cytotoxicity.