dimethyl 2,15-dibromo-3,3,14,14-tetramethyl-1,16-hexadecanedioate | 103198-99-8

• 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: dimethyl 2,15-dibromo-3,3,14,14-tetramethyl-1,16-hexadecanedioate
• 英文别名: dimethyl 2,15-dibromo-3,3,14,14-tetramethylhexadecanedioate；1,14-di-(carbomethoxy)-1,14-dibromo-2,2,13,13-tetramethyltetradecane
• CAS: 103198-99-8
• 化学式: C₂₂H₄₀Br₂O₄
• 分子量: 528.365
• InChiKey: MSTYEGBNWBXKEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2,15-dibromo-3,3,14,14-tetramethyl-1,16-hexadecanedioate 在 甲醇 、 硫酸 、 四丁基氟化铵 作用下， 反应 36.0h， 生成 2,15-difluoro-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：

  2,15-dibromo-3,3,14,14-tetramethyl hexadecane-1,16-dioyl chloride 以 甲醇 、 氯仿 为溶剂， 以40%的产率得到dimethyl 2,15-dibromo-3,3,14,14-tetramethyl-1,16-hexadecanedioate
  参考文献：
  名称：

  Long-chain .alpha.,.omega.-dicarboxylic acids and derivatives thereof

  摘要：

  一种新的化合物类别已经发现在体内有效地阻断胆固醇和中性脂质合成，而不会对能量代谢产生不良影响，对于治疗肥胖、高脂血症和成人发病型糖尿病非常有用。这些活性化合物具有一般结构式##STR1## 或其体内可水解的羧基官能衍生物，其中R.sub.1和R.sub.2分别独立地代表未取代或取代的烃基或杂环烷基基团；X和Y各自独立地代表氢、可选择取代的较低烷基、卤素、氰基、羧基、较低烷氧羰基或氨基甲酰基；Q代表由8至14个碳原子组成的线性链的双基团，其中一个或多个碳原子可以被杂原子取代，该链可选择地被惰性取代基取代，其中一个或多个碳或杂原子链成员可选择地构成环结构的一部分。

  公开号：

  US04689344A1

文献信息

• A facile synthesis of α,α,ω,ω-tetrahalo-α,ω-dicarboxylic esters
  作者：Yoelit Migron、Jochanan Blum、Jacob Bar-Tana

  DOI：10.1016/s0040-4020(01)89964-6

  日期：1987.1

  synthesis of some α,α,ω,ω-tetrachloro and tetrabromo-derivatives of the hypolipidemic 3,3,14,14-tetramethylhexadecanedioic acid from α,ω-dihalo-esters, carbon tetrahalides and lithium diisopropyl amide has been described. Interaction of α,ω-dichloro esters with CBr4 was shown to give the expected α,ω-dibromo-α,ω-dichloro compounds, but treatment of bis(l-methylethyl) 2,15-dibromo-3,3,14,14-tetramethyl

  已经描述了由α，ω-二卤代酯，四卤化碳和二异丙基氨基锂合成一些降血脂性3，3，14，14-四甲基十六烷二酸的α，α，ω，ω-四氯和四溴衍生物。研究表明，α，ω-二氯酯与CBr 4的相互作用产生了预期的α，ω-二溴-α，ω-二氯化合物，但处理了双（1-甲基乙基）2,15-dibromo-3,3,14发现具有CCl 4的14，4-四甲基六癸二酸酯导致卤素交换，产生四氯二酯作为主要产物。
• 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。
• Method of lowering CRP and reducing systemic inflammation
  申请人：——

  公开号：US20040167229A1

  公开（公告）日：2004-08-26

  Disclosed are methods of lowering plasma CRP levels, reducing systemic inflammation, and inhibiting proinflammatory cytokine induced CRP production by administering an effective amount of a substituted dialkyl ether, substituted alkyl, substituted aryl-alkyl, substituted dialkyl thioether, substituted dialkyl ketone, substituted-alkyl, or a pharmaceutically acceptable salt of the substituted dialkyl ether, substituted alkyl, substituted aryl-alkyl, substituted dialkyl thioether, substituted dialkyl ketone, or substituted-alkyl or a pharmaceutical composition comprising a substituted dialkyl ether, substituted alkyl, substituted aryl-alkyl, substituted dialkyl thioether, substituted dialkyl ketone, substituted-alkyl.

  本发明涉及通过给予有效量的取代二烷基醚、取代烷基、取代芳基-烷基、取代二烷基硫醚、取代二烷基酮、取代烷基或其药学上可接受的盐，以及包含取代二烷基醚、取代烷基、取代芳基-烷基、取代二烷基硫醚、取代二烷基酮、取代烷基的药物组合物，来降低血浆CRP水平，减少全身性炎症，并抑制促炎细胞因子诱导的CRP产生的方法。
• 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。
• Methods for treating inflammation and inflammation-associated diseases with a statin and ether
  申请人：Ghazzi Maha

  公开号：US20050026979A1

  公开（公告）日：2005-02-03

  Disclosed herein are methods for treating and preventing inflammation and inflammation-associated diseases by co-administering to a patient in need thereof 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 alkyl-alkyl, substituted dialkyl thioether, substituted dialkyl ketone, or substituted-alkyl, and a statin, or a pharmaceutically acceptable salt of said statin.

  本文公开了治疗和预防炎症和炎症相关疾病的方法，即向有需要的患者联合施用二烷基醚、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、取代的烷基-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，以及他汀类药物或所述他汀类药物的药学上可接受的盐。