tert-butyl 6-(phenylthio)hexanoate | 83836-81-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl 6-(phenylthio)hexanoate
• 英文别名: tert-butyl 6-phenylsulfanylhexanoate
• CAS: 83836-81-1
• 化学式: C₁₆H₂₄O₂S
• 分子量: 280.431
• InChiKey: SESUPTFTFURERV-UHFFFAOYSA-N

物化性质

• 沸点：
  362.5±25.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-(phenylthio)hexanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到6-苯基硫烷基己酸
  参考文献：
  名称：

  Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

  DOI：

  10.1021/jm061414r
• 作为产物：
  描述：

  6-溴己酸 在 硫酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 氯仿 、 苯 为溶剂， 反应 720.08h， 生成 tert-butyl 6-(phenylthio)hexanoate
  参考文献：
  名称：

  WO2008/150492

  摘要：

  公开号：

文献信息

• TRICYCLIC INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Boger Dale L.

  公开号：US20100216750A1

  公开（公告）日：2010-08-26

  A series of substituted oxazole compounds having an alpha keto side chain at the 2 position and an aromatic, heteroaromatic or heterocycle substituent at the 5 position are disclosed. These compounds exhibit inhibition of fatty acid amid hydrolase and arc useful for treatment of malconditions involving that enzyme.

  本发明揭示了一系列取代的噁唑化合物，其中在2位具有α-酮基侧链，在5位具有芳香、杂芳或杂环取代基。这些化合物表现出脂肪酸酰胺水解酶的抑制作用，并且对于治疗涉及该酶的恶性状况是有用的。
• US8124778B2
  申请人：——

  公开号：US8124778B2

  公开（公告）日：2012-02-28
• [EN] TRICYCLIC INHIBITORS OF FATTY ACID AMIDE HYDROLASE<br/>[FR] INHIBITEURS TRICYCLIQUES DE L'HYDROLASE AMIDE DES ACIDES GRAS FAAH
  申请人：BOGER DALE L

  公开号：WO2008150492A1

  公开（公告）日：2008-12-11

  [EN] A series of substituted oxazole compounds having an alpha keto side chain at the 2 position and an aromatic, heteroaromatic or heterocycle substituent at the 5 position are disclosed. These compounds exhibit inhibition of fatty acid amid hydrolase and are useful for treatment of malconditions involving that enzyme.
  [FR] La présente invention concerne une série de composés d'oxazole substitués comprenant une chaîne latérale alpha céto en position 2 et un substituant aromatique, hétéroaromatique ou hétérocyclique en position 5. Ces composés présentent une inhibition de l'enzyme FAAH et sont utiles pour le traitement de troubles impliquant cette enzyme.
• Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase
  作者：Christophe Hardouin、Michael J. Kelso、F. Anthony Romero、Thomas J. Rayl、Donmienne Leung、Inkyu Hwang、Benjamin F. Cravatt、Dale L. Boger

  DOI：10.1021/jm061414r

  日期：2007.7.1

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.
• WO2008/150492
  申请人：——

  公开号：——

  公开（公告）日：——