3-(6-bromohexyl)pyridine | 586976-81-0

• 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: 3-(6-bromohexyl)pyridine
• CAS: 586976-81-0
• 化学式: C₁₁H₁₆BrN
• 分子量: 242.159
• InChiKey: VISFTUCRZVRORW-UHFFFAOYSA-N

物化性质

• 沸点：
  322.6±25.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(6-bromohexyl)pyridine 在 potassium dihydrogenphosphate 、 sodium methylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.17h， 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 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 二异丁基氢化铝 、 dimsyl sodium 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 2.42h， 生成 3-(6-bromohexyl)pyridine
  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

• Total Synthesis and Assignment of the Double-Bond Position and Absolute Configuration of (−)-Pyrinodemin A
  作者：Yoshiki Morimoto、Satoru Kitao、Tatsuya Okita、Takamasa Shoji

  DOI：10.1021/ol034700v

  日期：2003.7.1

  see text] The first asymmetric total synthesis of a structurally novel cis-cyclopent[c]isoxazolidine alkaloid, (-)-pyrinodemin A (3), which exhibits potent cytotoxicity, has been accomplished through a highly diastereoselective intramolecular nitrone-olefin cycloaddition reaction as the key step. Thus, it has been found that the hitherto unknown absolute configuration of pyrinodemin A is as indicated

  [结构：见正文]结构上新颖的顺式环戊[c]异恶唑烷生物碱（-）-吡咯烷素A（3）的首次不对称全合成是通过高度非对映选择性的分子内硝酮-烯烃完成的，具有较强的细胞毒性。环加成反应是关键步骤。因此，发现迄今未知的嘧啶亚胺A的绝对构型如结构式3所示。
• <i>N</i>-Methylniphatyne A, a New 3-Alkylpyridine Alkaloid as an Inhibitor of the Cancer Cells Adapted to Nutrient Starvation, from an Indonesian Marine Sponge of <i>Xestospongia</i> sp.
  作者：Masayoshi Arai、Kentaro Kamiya、Dayoung Shin、Hirokazu Matsumoto、Tomoya Hisa、Andi Setiawan、Naoyuki Kotoku、Motomasa Kobayashi

  DOI：10.1248/cpb.c16-00118

  日期：——

  In the course of searching for selective growth inhibitors of the cancer cells adapted to nutrient starvation, a new 3-alkylpyridine alkaloid named N-methylniphatyne A (1) was isolated from an Indonesian marine sponge of Xestospongia sp. The chemical structure of 1 was determined on the basis of the spectroscopic analysis and comparison with the synthesized 1 and its analogues. Compound 1 showed the

  在寻找适合营养缺乏的癌细胞的选择性生长抑制剂的过程中，从印尼海洋海绵Xestospongia sp。分离出了一种新的3-烷基吡啶生物碱，名为N-methylniphatyne A（1）。1的化学结构是在光谱分析的基础上确定的，并与合成的1及其类似物进行比较。在葡萄糖饥饿的条件下，化合物1对PANC-1细胞具有细胞毒活性，IC50值为16 microM，而在一般培养条件下，直至100 microM都未观察到生长抑制作用。
• Pyrido(2,1-b)chinazolinderivate
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0094080B1

  公开（公告）日：1987-09-09
• US4551460A
  申请人：——

  公开号：US4551460A

  公开（公告）日：1985-11-05
• 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.