4-tert-Butyl-cyclohexan-carbonsaeure-1-essigsaeure-(1) | 93428-10-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-tert-Butyl-cyclohexan-carbonsaeure-1-essigsaeure-(1)
• 英文别名: 4-Tert-butyl-1-(carboxymethyl)cyclohexane-1-carboxylic acid
• CAS: 93428-10-5
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: JJHVWOZPIWMPGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tert-Butyl-cyclohexan-carbonsaeure-1-essigsaeure-(1) 在 乙酸酐 作用下， 反应 4.0h， 生成 8-tert-butyl-2-oxa-spiro[4.5]decane-1,3-dione
  参考文献：
  名称：

  Antiarthritic and supressor cell inducing activity of azaspiranes: structure-function relationships of a novel class of immunomodulatory agents

  摘要：

  Spirogermanium (1; 8,8-diethyl-N,N-dimethyl-2-aza-8- germaspiro[4.5]decane-2-propanamine dihydrochloride) is a potent cytotoxic agent in vitro which has demonstrated limited activity in experimental animal tumor models. Subsequently, it has been reported that spirogermanium has antiarthritic and suppressor cell-inducing activity. We have synthesized a series of substituted 8-hetero-2-azaspiro[4.5]decane and 9-hetero-3-azaspiro[5.5]undecane analogues of spirogermanium to identify the heteroatom requirements for in vivo antiarthritic and suppressor cell-inducing activity. This structure-activity relationship study has identified that appropriately substituted silicon and carbon analogues of spirogermanium retain both antiarthritic and immunosuppressive activity, with the 8,8-dipropyl (carbon) analogue being among the most active. Following the identification of N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride (9) as a more active analogue than spirogermanium, a series of 8,8-dipropyl analogues with various amine substituents were synthesized. A number of these analogues had activity similar to that of 9. A correlation between activity in the adjuvant arthritic rat and the ability to induce suppressor cells (r = 0.894, p less than 0.001) suggests an association between the two pharmacologic effects. While the precise biochemical mechanism(s) for the pharmacological activity is unclear, these data suggest that compounds within this series, e.g., N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride, may provide effective therapy in diseases of autoimmune origin and/or the prevention of rejection in tissue transplantation.

  DOI：

  10.1021/jm00173a010
• 作为产物：
  描述：

  ethyl (4-t-butylcyclohexylidene)cyanoacetate 在 盐酸 、 potassium cyanide 作用下， 生成 4-tert-Butyl-cyclohexan-carbonsaeure-1-essigsaeure-(1)
  参考文献：
  名称：

  Spiranes 6. N-苄氧基-2-氮杂螺[4.4]壬烷-1,3-二酮的A环同系物。合成，X射线分析和抗惊厥评估。

  摘要：

  合成了一系列螺琥珀酰亚胺，并评估了其抗惊厥活性。该研究旨在确定在维持杂环恒定的同时改变碳环（环A）核对抗惊厥活性的影响。结果表明，环A包含六元螺环系统2a，比先前报道的N-（苄氧基）-2-氮杂螺[4.4]壬烷-1,3-所报道的亚甲基大，获得的最大活性。 dione，1，原型类似物。化合物2a在MES测试中具有活性，并提供100 mg / kg的保护，螺十二烷类似物2g也是如此。X射线分析显示，活性2a和非活性螺辛烷类似物2f之间存在显着差异。但是，这些差异不能解释螺十二烷类似物2g表现出的意外活性。

  DOI：

  10.1016/0223-5234(96)83972-9

文献信息

• Picard, Philippe; Moulines, Jean; Lecoustre, Max, Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 65 - 70
  作者：Picard, Philippe、Moulines, Jean、Lecoustre, Max

  DOI：——

  日期：——
• Stereochemistry of 1,4-addition of nucleophiles to ethyl cyclohexylidenecyanoacetates
  作者：Dhanonjoy Nasipuri、Ashis Sarkar、Samir K. Konar

  DOI：10.1021/jo00136a004

  日期：1982.7
• Stanetty, Peter; Kasemann, Olaf; Mihvilovic, Marko D., Scientia Pharmaceutica, 1996, vol. 64, # 3-4, p. 669 - 677
  作者：Stanetty, Peter、Kasemann, Olaf、Mihvilovic, Marko D.

  DOI：——

  日期：——
• BADGER, ALISON M.;CHEESEMAN, ELAINE N.;DIMARTINO, MICHAEL J.;DORMAN, JAME+
  作者：BADGER, ALISON M.、CHEESEMAN, ELAINE N.、DIMARTINO, MICHAEL J.、DORMAN, JAME+

  DOI：——

  日期：——
• NASIPURI, D.;SARKAR, A.;KONAR, S. K., J. ORG. CHEM., 1982, 47, N 15, 2840-2845
  作者：NASIPURI, D.、SARKAR, A.、KONAR, S. K.

  DOI：——

  日期：——