2-(7-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-8-methoxy-1,6-naphthyridin-5-yl)-1,2-thiazinane 1,1-dioxide | 1153775-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(7-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-8-methoxy-1,6-naphthyridin-5-yl)-1,2-thiazinane 1,1-dioxide
• CAS: 1153775-15-5
• 化学式: C₂₂H₂₀FN₅O₄S
• 分子量: 469.496
• InChiKey: RTCCRSSATXHMEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  111.31
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(7-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-8-methoxy-1,6-naphthyridin-5-yl)-1,2-thiazinane 1,1-dioxide 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以93%的产率得到
  参考文献：
  名称：

  The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore

  摘要：

  A series of HIV-1 integrase inhibitors containing a novel metal binding motif consisting of the 8-hydroxy1,6-naphthyridine core and either an oxadiazole or triazole has been identified. The design of the key structural components was based on a two-metal coordination pharmacophore. This report presents initial structure-activity data that shows the new chelation architecture delivers potent inhibition in both enzymatic and antiviral assays. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.090
• 作为产物：
  描述：

  5-(1,1-dioxido-1,2-thiazinan-2-yl)-N'-(2-(4-fluorophenyl)acetyl)-8-methoxy-1,6-naphthyridine-7-carbohydrazide 在 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到2-(7-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-8-methoxy-1,6-naphthyridin-5-yl)-1,2-thiazinane 1,1-dioxide
  参考文献：
  名称：

  The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore

  摘要：

  A series of HIV-1 integrase inhibitors containing a novel metal binding motif consisting of the 8-hydroxy1,6-naphthyridine core and either an oxadiazole or triazole has been identified. The design of the key structural components was based on a two-metal coordination pharmacophore. This report presents initial structure-activity data that shows the new chelation architecture delivers potent inhibition in both enzymatic and antiviral assays. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.090

文献信息

• 1,3,4-Oxadiazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 2: SAR of the C5 position
  作者：Brian A. Johns、Jason G. Weatherhead、Scott H. Allen、James B. Thompson、Edward P. Garvey、Scott A. Foster、Jerry L. Jeffrey、Wayne H. Miller

  DOI：10.1016/j.bmcl.2009.01.089

  日期：2009.3

  The use of a 1,3,4-oxadiazole in combination with an 8-hydroxy-1,6-naphthyridine ring system has been shown to deliver potent enzyme and antiviral activity through inhibition of viral DNA integration. This report presents a detailed structure-activity investigation of the C5 position resulting in low nM potency for several analogs with an excellent therapeutic index. (C) 2009 Elsevier Ltd. All rights reserved.