1,14-di-(ethoxycarbonyl)-1,14-dicyano-2,2,13,13-tetramethyl-tetradecane | 87272-23-9

• 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: 1,14-di-(ethoxycarbonyl)-1,14-dicyano-2,2,13,13-tetramethyl-tetradecane
• 英文别名: Diethyl 2,15-dicyano-3,3,14,14-tetramethylhexadecanedioate
• CAS: 87272-23-9
• 化学式: C₂₆H₄₄N₂O₄
• 分子量: 448.646
• InChiKey: UGOLGVFRZXYQSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,14-di-(ethoxycarbonyl)-1,14-dicyano-2,2,13,13-tetramethyl-tetradecane 在 氢氧化钾 作用下， 以 水 为溶剂， 以97%的产率得到2,15-dicyano-3,3,14,14-tetramethylhexadecanedioic acid
  参考文献：
  名称：

  Synthesis and hypolipidemic and antidiabetogenic activities of .beta.,.beta.,.beta.',.beta.'-tetrasubstituted, long-chain dioic acids

  摘要：

  beta,beta,beta',beta'-Tetrasubstituted, long-chain dioic acids of the general formula HOOC-C(XY)-C(R2)-Q-C-(R2)-C(XY)-COOH have been synthesized and evaluated as hypotriglyceridemic-hypocholesterolemic agents in rats and as antidiabetogenic agents in ob/ob diabetic mice. The free carboxyl function of analogues of the series was mandatory for their hypolipidemic-antidiabetogenic effect while nonhydrolyzable diesters were inactive. Other structure-activity relationships were determined as a function of the overall chain length (C12-C22), alpha,alpha'-substitutions (X, Y = H, F, Cl, Br, OH, CN), beta, beta'-substitutions (R = CH3, C6H5), and core substitutions [Q = (CH2)10, (CH2)4CH = CH(CH2)4, 1,4-C6H10[(CH2)3]2, 1,4-C6H4[(CH2)3]2, 1,4-C6H4(CH = CHCH2)2, CH2(OCH2CH2)3OCH2)]. The most effective hypolipidemic-antidiabetogenic members of the series were alpha,alpha'-nonsubstituted, beta,beta'-methyl-substituted analogues of 14-18-carbon chains having either a saturated aliphatic core or a 1,4-bis(propenyl)benzene core in the cis/trans configuration. The hypotriglyceridemic rather than the hypocholesterolemic capacity of members of the series was found to correlate with their respective capacities as liver peroxisomal proliferators in rats.

  DOI：

  10.1021/jm00129a010
• 作为产物：
  描述：

  1,10-Decandiylbis(magnesiumbromid) 、 2-氰基-3-甲基丁烯酸乙酯 在 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以28%的产率得到1,14-di-(ethoxycarbonyl)-1,14-dicyano-2,2,13,13-tetramethyl-tetradecane
  参考文献：
  名称：

  Synthesis and hypolipidemic and antidiabetogenic activities of .beta.,.beta.,.beta.',.beta.'-tetrasubstituted, long-chain dioic acids

  摘要：

  beta,beta,beta',beta'-Tetrasubstituted, long-chain dioic acids of the general formula HOOC-C(XY)-C(R2)-Q-C-(R2)-C(XY)-COOH have been synthesized and evaluated as hypotriglyceridemic-hypocholesterolemic agents in rats and as antidiabetogenic agents in ob/ob diabetic mice. The free carboxyl function of analogues of the series was mandatory for their hypolipidemic-antidiabetogenic effect while nonhydrolyzable diesters were inactive. Other structure-activity relationships were determined as a function of the overall chain length (C12-C22), alpha,alpha'-substitutions (X, Y = H, F, Cl, Br, OH, CN), beta, beta'-substitutions (R = CH3, C6H5), and core substitutions [Q = (CH2)10, (CH2)4CH = CH(CH2)4, 1,4-C6H10[(CH2)3]2, 1,4-C6H4[(CH2)3]2, 1,4-C6H4(CH = CHCH2)2, CH2(OCH2CH2)3OCH2)]. The most effective hypolipidemic-antidiabetogenic members of the series were alpha,alpha'-nonsubstituted, beta,beta'-methyl-substituted analogues of 14-18-carbon chains having either a saturated aliphatic core or a 1,4-bis(propenyl)benzene core in the cis/trans configuration. The hypotriglyceridemic rather than the hypocholesterolemic capacity of members of the series was found to correlate with their respective capacities as liver peroxisomal proliferators in rats.

  DOI：

  10.1021/jm00129a010

文献信息

• Method of treating osteoarthritis
  申请人：——

  公开号：US20040048910A1

  公开（公告）日：2004-03-11

  This invention relates to combinations, compositions, and methods using or having a substituted dialkyl ether, substituted aryl-alkyl ether, substituted dialkyl thioether, substituted dialkyl ketone, or substituted-alkyl compound, or a pharmaceutically acceptable salt thereof, as an active component for preventing or treating osteoarthritis, preventing or inhibiting cartilage damage, preventing or treating rheumatoid arthritis, improving joint function, alleviating pain, and the like in a patient in need thereof.

  本发明涉及使用或含有取代的二烷基醚、取代的芳基-烷基醚、取代的二烷基硫醚、取代的二烷基酮或取代的烷基化合物，或其药学上可接受的盐作为活性成分，用于预防或治疗骨关节炎、预防或抑制软骨损伤、预防或治疗类风湿关节炎、改善关节功能、缓解疼痛等方面的组合物、组成物和方法，适用于需要治疗的患者。
• Long-chain alpha, omega-dicarboxylic acids and derivatives thereof and pharmaceutical compositions containing them
  申请人：Epis S.A.

  公开号：EP0081930A1

  公开（公告）日：1983-06-22

  A novel class of compounds has been found to be effective in blocking cholesterol and neutral lipid synthesis n-vivo without adversely affecting energy metabolism. The active compounds have the general formula or in-vivo hydrolysable functional derivatives of the carboxylic groups thereof, wherein R1 and R2 each independently represents an unsubstituted or substituted hydrocarbyl or heterocyclyl radical; X and Y each independently represents hydrogen, optionally substituted lower alkyl, halogen, cyano, carboxy, lower alkoxycarbonyl or carbamoyl; and Q represents a diradical consisting of a linear chain of 8 to 14 carbon atoms, one or more of which may be replaced by heteroatoms, said chain being optionally substituted by inert substituents and one or more of said carbon or heteroatom chain members optionally forming part of a ring structure. The invention also provides pharmaceutical compositions comprising the aforementioned compounds of formula (I) for the treatment of obesity, hyperlipidemia and- maturity-onset diabetes.

  研究发现，一类新型化合物能有效阻止体内胆固醇和中性脂质的合成，而不会对能量代谢产生不利影响。这些活性化合物的通式为 或其羧基的体内可水解官能团衍生物，其中 R1 和 R2 各自独立地代表未取代或取代的烃基或杂环基； X和Y各自独立地代表氢、任选取代的低级烷基、卤素、氰基、羧基、低级烷氧基羰基或氨基甲酰基；以及 Q 代表由 8 至 14 个碳原子的线性链组成的二叉基，其中一个或多个碳原子可被杂原子取代，所述链可任选被惰性取代基取代，一个或多个所述碳或杂原子链成员可任选形成环状结构的一部分。 本发明还提供了包含上述式（I）化合物的药物组合物，用于治疗肥胖症、高脂血症和成熟期糖尿病。
• Pharmaceutical compositions including an ether and selective COX-2 inhibitor and methods for using such
  申请人：Kowala C. Mark

  公开号：US20050004196A1

  公开（公告）日：2005-01-06

  Disclosed herein are pharmaceutical compositions including a dialkyl ether, substituted alkyl, substituted aryl-alkyl, substituted dialkyl thioether, substituted dialkyl ketone, substituted-alkyl, or a pharmaceutically acceptable salt of said dialkyl ether, substituted alkyl, substituted aryl-alkyl, substituted dialkyl thioether, substituted dialkyl ketone, or substituted-alkyl, and a selective cyclooxygenase-2 (COX-2) inhibitor, or a pharmaceutically acceptable salt of said selective COX-2 inhibitor. Also disclosed are methods of using such pharmaceutical compositions for the treatment of inflammation and inflammation-associated diseases, inflammation and inflammation-associated disorders mediated by proinflammatory cytokines, and proinflammatory cytokine induced CRP production.

  本文公开了药物组合物，包括二烷基醚、取代的烷基、取代的芳基烷基、取代的二烷基硫醚、取代的二烷基酮、取代的烷基或所述二烷基醚、取代的烷基、取代的芳基烷基、取代的二烷基硫醚、取代的二烷基酮或取代的烷基的药学上可接受的盐，以及选择性环氧化酶-2（COX-2）抑制剂或所述选择性COX-2抑制剂的药学上可接受的盐。还公开了使用此类药物组合物治疗炎症和炎症相关疾病、由促炎细胞因子介导的炎症和炎症相关疾病以及促炎细胞因子诱导的 CRP 生成的方法。
• BAR-TANA, JACOB;BEN-SHOSHAN, SHOSHANA;BLUM, JOCHANAN;MIGRON, YOELIT;HERTZ+, J. MED. CHEM., 32,(1989) N, C. 2072-2084
  作者：BAR-TANA, JACOB、BEN-SHOSHAN, SHOSHANA、BLUM, JOCHANAN、MIGRON, YOELIT、HERTZ+

  DOI：——

  日期：——
• US4689344A
  申请人：——

  公开号：US4689344A

  公开（公告）日：1987-08-25