trans-methanesulfonic acid 4-(2-methylaminoethyl)cyclohexylmethyl ester hydrochloride | 554455-00-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trans-methanesulfonic acid 4-(2-methylaminoethyl)cyclohexylmethyl ester hydrochloride
• 英文别名: trans-methanesulfonic acid 4-(2-methylamino-ethyl)-cyclohexylmethyl ester HCl salt
• CAS: 554455-00-4
• 化学式: C₁₁H₂₃NO₃S*ClH
• 分子量: 285.835
• InChiKey: MONVMMPPZSUNCA-PFWPSKEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-methanesulfonic acid 4-(2-methylaminoethyl)cyclohexylmethyl ester hydrochloride 在 硫酸二甲酯 作用下， 以 乙酸乙酯 、 二甲胺 、 异丙醇 、 乙腈 为溶剂， 反应 123.0h， 生成 trans-[2-(4-{[ethyl-(2-hydroxyethyl)amino]methyl}cyclohexyl)ethyl]methylmethylcarbamic acid 4-trifluoromethylphenyl ester citrate
  参考文献：
  名称：

  Cytotoxic Effects of Combination of Oxidosqualene Cyclase Inhibitors with Atorvastatin in Human Cancer Cells

  摘要：

  Ten oxidosqualene c-yclase inhibitors with high efficacy as cholesterol-lowering agents and of different chemical structure classes were evaluated as potential anticancer agents against human cancer cells from various tissue origins and nontumoral human-brain-derived endothelial cells. Inhibition of cancer cell growth was demonstrated at micromolar concentrations, comparable to the concentrations of statins necessary for antitumor effect. Human glioblastoma cells were among the most sensitive cells. These compounds were also able to decrease the proliferation of angiogenic brain-derived endothelial cells, as a model of tumor-induced neovasculation. Additive effects in human glioblastoma cells were also demonstrated for oxidosqualene cyclase inhibitors in combination with atorvastatin while maintaining selectivity against endothelial cells. Thus, not only statins targeting the 3-hydroxy-3-methylglutaryl coenzyme A reductase but also inhibitors of oxidosqualene cyclase decrease tumor growth, suggesting new therapeutic opportunities of combined anti-cholesterol agents for dual treatment of glioblastoma.

  DOI：

  10.1021/jm300256z
• 作为产物：
  描述：

  trans-acetic acid 4-(2-(tert-butoxycarbonylamino)ethyl)cyclohexylmethyl ester 在 盐酸 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 trans-methanesulfonic acid 4-(2-methylaminoethyl)cyclohexylmethyl ester hydrochloride
  参考文献：
  名称：

  Cytotoxic Effects of Combination of Oxidosqualene Cyclase Inhibitors with Atorvastatin in Human Cancer Cells

  摘要：

  Ten oxidosqualene c-yclase inhibitors with high efficacy as cholesterol-lowering agents and of different chemical structure classes were evaluated as potential anticancer agents against human cancer cells from various tissue origins and nontumoral human-brain-derived endothelial cells. Inhibition of cancer cell growth was demonstrated at micromolar concentrations, comparable to the concentrations of statins necessary for antitumor effect. Human glioblastoma cells were among the most sensitive cells. These compounds were also able to decrease the proliferation of angiogenic brain-derived endothelial cells, as a model of tumor-induced neovasculation. Additive effects in human glioblastoma cells were also demonstrated for oxidosqualene cyclase inhibitors in combination with atorvastatin while maintaining selectivity against endothelial cells. Thus, not only statins targeting the 3-hydroxy-3-methylglutaryl coenzyme A reductase but also inhibitors of oxidosqualene cyclase decrease tumor growth, suggesting new therapeutic opportunities of combined anti-cholesterol agents for dual treatment of glioblastoma.

  DOI：

  10.1021/jm300256z

文献信息

• Substituted cyclohexane derivatives
  申请人：——

  公开号：US20030199550A1

  公开（公告）日：2003-10-23

  The present invention provides compounds of formula (I) 1 wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , A 10 , U, V, W, m, n and p are as indicated in the specification, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia and hyperlipemia.

  本发明提供了以下式(I)1的化合物，其中A1、A2、A3、A4、A5、A6、A7、A8、A9、A10、U、V、W、m、n和p如规范中所示，并其药学上可接受的盐。这些化合物可用于治疗和/或预防与2,3-氧化甾二烯-鲑鲈固醇环化酶相关的疾病，如高胆固醇血症和高脂血症。
• SUBSTITUTED CYCLOHEXANE DERIVATIVES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1456171B1

  公开（公告）日：2006-12-20
• US6953806B2
  申请人：——

  公开号：US6953806B2

  公开（公告）日：2005-10-11
• [EN] SUBSTITUTED CYCLOHEXANE DERIVATIVES<br/>[FR] DERIVES SUBSTITUES DU CYCLOHEXANE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003053919A1

  公开（公告）日：2003-07-03

  The present invention relates to compounds of formula (I) wherein A?1, A2, A3, A4, A5, A6, A7, A8, A9, A10¿, U, V, W, m, n and p are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, parasit infections, gallstones, tumors and/or hyperproliferative disorders, and treatment and/or prophylaxis of impaired glucose tolerance and diabetes.