11-cyclohexylideneundecanoic acid methyl ester | 503868-34-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11-cyclohexylideneundecanoic acid methyl ester
• 英文别名: methyl 11-(cyclohexylidene)undecanoate；Methyl 11-cyclohexylideneundecanoate
• CAS: 503868-34-6
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: KCUTVECERBDCKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-cyclohexylideneundecanoic acid methyl ester 在 palladium on charcoal 作用下， 以 四氢呋喃 为溶剂， 生成 methyl ω-cyclohexylundecanoate
  参考文献：
  名称：

  Pentanedioic acid derivatives

  摘要：

  描述了一种化学式I的化合物，它们通过抑制其对抑制β-羟基-β-甲基戊二酰辅酶A（HMG CoA）的能力，有助于抑制血清胆固醇的形成。HMG CoA是血清胆固醇合成中的速率控制物质。

  公开号：

  US04645858A1
• 作为产物：
  描述：

  环己酮 、 10-carbomethoxydecyltriphenylphosphonium bromide 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 以79%的产率得到11-cyclohexylideneundecanoic acid methyl ester
  参考文献：
  名称：

  Antileishmanial Ring-Substituted Ether Phospholipids

  摘要：

  Three series of ring-substituted ether phospholipids were synthesized carrying N,N,N-trimethylammonium, N-methylpiperidino, or N-methylmorpholino headgroups. The first series is substituted by 2-cyclohexyloxyethyl or 2-(4-alkylidenecyclohexyloxy)ethyl groups, the second series by cyclohexylidenealkyl or adamantylidenealkyl moieties, and the third series by 2-aryloxyethyl or 6-aryloxyhexyl groups in the alkyl portion of the molecule. The antileishmanial activity of the new compounds was evaluated in vitro against the promastigote forms of L. donovani and L. infantum using an MTT (3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide)-based microassay as a marker of cell viability. Analogues 12, 15, 24, 30, 32, 41, 43, and 45 were more potent than the control compound miltefosine (hexadecylphosphocholine) against both L. donovani and L. infantum while, derivatives 13 and 42 were equipotent to miltefosine. Analogues 16, 17, 19, 20 were more potent than miltefosine against L. infantum and compounds 27, 31, 44 were more active than miltefosine against L. donovani. Differential scanning calorimetry (DSC) was used to probe the role of individual ether phospholipids on the physicochemical properties of model membranes. The DSC scans showed that the active compounds have a more profound effect on the thermotropic properties of model membrane bilayers than the less active ones.

  DOI：

  10.1021/jm020972c

文献信息

• ——
  作者：LOWRIE H. S.、 BARAN J. S.

  DOI：——

  日期：——
• US4645858A
  申请人：——

  公开号：US4645858A

  公开（公告）日：1987-02-24
• Antileishmanial Ring-Substituted Ether Phospholipids
  作者：Nikos Avlonitis、Eleni Lekka、Anastasia Detsi、Maria Koufaki、Theodora Calogeropoulou、Efi Scoulica、Eleni Siapi、Ioanna Kyrikou、Thomas Mavromoustakos、Andrew Tsotinis、Simona Golic Grdadolnik、Alexandros Makriyannis

  DOI：10.1021/jm020972c

  日期：2003.2.1

  Three series of ring-substituted ether phospholipids were synthesized carrying N,N,N-trimethylammonium, N-methylpiperidino, or N-methylmorpholino headgroups. The first series is substituted by 2-cyclohexyloxyethyl or 2-(4-alkylidenecyclohexyloxy)ethyl groups, the second series by cyclohexylidenealkyl or adamantylidenealkyl moieties, and the third series by 2-aryloxyethyl or 6-aryloxyhexyl groups in the alkyl portion of the molecule. The antileishmanial activity of the new compounds was evaluated in vitro against the promastigote forms of L. donovani and L. infantum using an MTT (3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide)-based microassay as a marker of cell viability. Analogues 12, 15, 24, 30, 32, 41, 43, and 45 were more potent than the control compound miltefosine (hexadecylphosphocholine) against both L. donovani and L. infantum while, derivatives 13 and 42 were equipotent to miltefosine. Analogues 16, 17, 19, 20 were more potent than miltefosine against L. infantum and compounds 27, 31, 44 were more active than miltefosine against L. donovani. Differential scanning calorimetry (DSC) was used to probe the role of individual ether phospholipids on the physicochemical properties of model membranes. The DSC scans showed that the active compounds have a more profound effect on the thermotropic properties of model membrane bilayers than the less active ones.
• Pentanedioic acid derivatives
  申请人：G. D. Searle & Co.

  公开号：US04645858A1

  公开（公告）日：1987-02-24

  Compounds of formula I are described which are useful to inhibit the formation of serum cholesterol by virtue of their ability to inhibit .beta.-hydroxy-.beta.-methylglutaryl-CoA(HMG CoA), the rate-controlling substance in the synthesis of serum cholesterol.

  描述了一种化学式I的化合物，它们通过抑制其对抑制β-羟基-β-甲基戊二酰辅酶A（HMG CoA）的能力，有助于抑制血清胆固醇的形成。HMG CoA是血清胆固醇合成中的速率控制物质。