6-(3-Pyridinyl)-5-hexen-1-ol | 138745-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(3-Pyridinyl)-5-hexen-1-ol
• 英文别名: 6-pyridin-3-ylhex-5-en-1-ol
• CAS: 138745-77-4
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: BBVMJBHNZSHUIE-UHFFFAOYSA-N

物化性质

• 沸点：
  336.8±35.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(3-Pyridinyl)-5-hexen-1-ol 在 platinum(IV) oxide potassium dihydrogenphosphate 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 38.59h， 生成 Methyl 3-cyano-3-hydroxy-4-(6-pyridin-3-ylhexylsulfanyl)butanoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 二异丁基氢化铝 、 dimsyl sodium 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 6-(3-Pyridinyl)-5-hexen-1-ol
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w

文献信息

• [EN] NEW BHT ETHER COMPOUNDS AND THEIR USE AS HYPOLIPIDEMIC AND ANTIATHEROSCLEROTIC DRUGS
  申请人：MERZ + CO., GMBH & CO.

  公开号：WO1993012089A1

  公开（公告）日：1993-06-24

  (EN) Pharmaceutically-active BHT-omega pyridyl ethers of the formula selected from BHT-omega-pyridyl ether compounds of formula (I) wherein -3-Pyr = (a), wherein m = 1,3, for m = 1, $g(S) = 6 - 9, for m = 3, $g(S) = 5 - 11, Sum ($g(S)) = [m+n+1 (for oxygen)] wherein the bond between the two carbon atoms of the (CHp)n moiety most closely adjacent the pyridine ring is a single, double, or triple bond, and p is 0, 1 or 2, depending on the type of bond, and pharmaceutically-acceptable acid addition salts thereof, pharmaceutical compositions thereof, and a method of combating lipidemia and atherosclerosis therewith, are disclosed.(FR) Ethers BHT-omega pyridyle à effet pharmaceutique de la formule choisie parmi les composés d'éther BHT-omega pyridyle de la formule (I) dans laquelle -3-Pyr = (a), dans laquelle m = 1,3 pour m = 1, $g(S) = 6 - 9, pour m = 3, $g(S) = 5 - 11, somme ($g(S)) = [m+n+1 (pour l'oxygène)] dans laquelle la liaison entre les deux atomes de carbone de la moitié (CHp)n la plus étroitement adjacente à la boucle pyridine est une liaison unique, double ou triple, leurs sels d'addition acides à effet pharmaceutique, compositions pharmaceutiques issues des précédents et procédé d'intervention contre la lipidémie et l'athérosclérose.

  具有药物活性的BHT-ω-吡啶醚的化学式选自化合物式(I)的BHT-ω-吡啶醚化合物，其中-3-Pyr=(a)，其中m=1,3，对于m=1，$g(S)=6-9，对于m=3，$g(S)=5-11，Sum($g(S))=[m+n+1(对于氧)]，其中(CHp)n基团的两个碳原子与吡啶环最接近的键是单键、双键或三键，p取决于化学键的类型，可以为0、1或2，并且其药学上可接受的酸加成盐、制剂以及用于对抗脂质血症和动脉粥样硬化的方法也被揭示。
• NEW BHT ETHER COMPOUNDS AND THEIR USE AS HYPOLIPIDEMIC AND ANTIATHEROSCLEROTIC DRUGS
  申请人：MERTZ + CO., GMBH & CO

  公开号：EP0619807A1

  公开（公告）日：1994-10-19
• US5254549A
  申请人：——

  公开号：US5254549A

  公开（公告）日：1993-10-19
• US5428168A
  申请人：——

  公开号：US5428168A

  公开（公告）日：1995-06-27
• ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme
  作者：Andrew D. Gribble、Roland E. Dolle、Antony Shaw、David McNair、Riccardo Novelli、Christine E. Novelli、Brian P. Slingsby、Virendra P. Shah、David Tew、Barbara A. Saxty、Mark Allen、Pieter H. Groot、Nigel Pearce、John Yates

  DOI：10.1021/jm960167w

  日期：1996.1.1

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.