5-pentyl-2,4-decadienoic acid | 122214-04-4

• 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: 5-pentyl-2,4-decadienoic acid
• 英文别名: (2E)-5-pentyldeca-2,4-dienoic acid
• CAS: 122214-04-4
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: DINOVIMWJXUKNN-UKTHLTGXSA-N

物化性质

• 沸点：
  368.7±11.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-pentyl-2,4-decadienoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-5-Pentyl-deca-2,4-dienoic acid ((R)-1-methyl-4-pyridin-3-yl-butyl)-amide
  参考文献：
  名称：

  Pentadienyl carboxamide derivatives as antagonists of platelet activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl]-5,5-disubstituted-pentadienamides was prepared and evaluated for PAF-antagonist activity. Compounds were assayed in vitro in a PAF-binding assay employing washed, whole dog platelets as the receptor source and in vivo after intravenous or oral administration for their ability to prevent PAF-induced bronchoconstriction in guinea pigs. Criteria required for good oral activity in the latter model include an (E,-E)-5-phenyl-2,4-pentadienamide, a second phenyl or a four- or five-carbon alkyl moiety in the 5-position of the diene, and an (R)-[1-alkyl-4-(3-pyridinyl)butyl] substituent on the carboxamide nitrogen atom. The alkyl substituent on this side chain can be methyl, ethyl, or cyclopropyl. Two members of this series, [R-(E)]-5,5-bis(4-methoxy-phenyl)-N- [1-methyl-4-(3-pyridinyl)butyl]- 2,4-pentadienamide (31) and [R-(E,E)]-5-(4-methoxyphenyl)-N-[1-methyl-4- (3-pyridinyl)butyl]-2,4-decadienamide (58), were selected for further pharmacological evaluation. Both were found to be substantially longer acting after oral administration than the corresponding S enantiomers in the guinea pig bronchoconstriction assay. A second in vivo model used to evaluate PAF antagonists determines the ability of test compounds to decrease the area of skin wheals induced by an intradermal injection of PAF. In this model, using both rats and guinea pigs, compounds 31 and 58 were found to be as active as the reference PAF antagonist 3-[4-(2-chlorophenyl)-9-methyl-6H- 1-(4-morpholinyl)-1-propanone (45).

  DOI：

  10.1021/jm00128a026
• 作为产物：
  描述：

  二正戊基酮 在 sodium hydroxide 作用下， 反应 0.5h， 生成 5-pentyl-2,4-decadienoic acid
  参考文献：
  名称：

  Pentadienyl carboxamide derivatives as antagonists of platelet activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl]-5,5-disubstituted-pentadienamides was prepared and evaluated for PAF-antagonist activity. Compounds were assayed in vitro in a PAF-binding assay employing washed, whole dog platelets as the receptor source and in vivo after intravenous or oral administration for their ability to prevent PAF-induced bronchoconstriction in guinea pigs. Criteria required for good oral activity in the latter model include an (E,-E)-5-phenyl-2,4-pentadienamide, a second phenyl or a four- or five-carbon alkyl moiety in the 5-position of the diene, and an (R)-[1-alkyl-4-(3-pyridinyl)butyl] substituent on the carboxamide nitrogen atom. The alkyl substituent on this side chain can be methyl, ethyl, or cyclopropyl. Two members of this series, [R-(E)]-5,5-bis(4-methoxy-phenyl)-N- [1-methyl-4-(3-pyridinyl)butyl]- 2,4-pentadienamide (31) and [R-(E,E)]-5-(4-methoxyphenyl)-N-[1-methyl-4- (3-pyridinyl)butyl]-2,4-decadienamide (58), were selected for further pharmacological evaluation. Both were found to be substantially longer acting after oral administration than the corresponding S enantiomers in the guinea pig bronchoconstriction assay. A second in vivo model used to evaluate PAF antagonists determines the ability of test compounds to decrease the area of skin wheals induced by an intradermal injection of PAF. In this model, using both rats and guinea pigs, compounds 31 and 58 were found to be as active as the reference PAF antagonist 3-[4-(2-chlorophenyl)-9-methyl-6H- 1-(4-morpholinyl)-1-propanone (45).

  DOI：

  10.1021/jm00128a026

文献信息

• Pentadieneamides
  申请人：Hoffmann-La Roche Inc.

  公开号：US04788206A1

  公开（公告）日：1988-11-29

  Compounds of the formula ##STR1## Y is O ir S, *A is paraphenylene or *----(CH.sub.2)n----(X).sub.m --(CH.sub.2).sub.r ----, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het, aryl, R.sub.3, R.sub.4 and R.sub.8, independently, are hydrogen, lower alkyl, aryl, R.sub.5 and R.sub.6, independently, are hydrogen or lower alkyl, R.sub.7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment, and when R.sub.6 and R.sub.7 are different, their enantiomers and racemic mixtures thereof, when R.sub.1 and R.sub.2 are different, their geometric isomers, and pharmaceutically acceptable acid addition salts thereof, are described. The compounds of formula I exhibit activity as platelet activating factor (PAF) antagonists and are, therefore, useful in disease states characerized by excess platelet activating factor or for the prevention and treatment of cardiovascular disease, pulmonary diseases, immunological disorders, inflammatory diseases, dermatological disorders, shock or transplant rejection.

  公式为##STR1##的化合物。其中Y为O或S，*A为对苯基或*----(CH.sub.2)n----(X).sub.m --(CH.sub.2).sub.r ----，X为O、S或--CH.dbd.CH--，n或r独立地为0到3的整数，s为0到1的整数，m为0到1的整数，但当m为1时，n+s必须至少为2，R.sub.1和R.sub.2独立地为氢、低烷基、环烷基、低烯基、Het、芳基，R.sub.3、R.sub.4和R.sub.8独立地为氢、低烷基、芳基，R.sub.5和R.sub.6独立地为氢或低烷基，R.sub.7为氢、低烷基、环烷基、Het-低烷基或芳基，Het为含有一或两个从氮、氧和硫中选择的杂原子的单环5-或6-成员杂芳基或含有一个或两个杂原子的双环杂芳基，该基团可以被低烷基、卤素或芳基取代，星号表示连接点，当R.sub.6和R.sub.7不同时，它们的对映异构体和消旋混合物，当R.sub.1和R.sub.2不同时，它们的几何异构体以及其药学上可接受的酸盐被描述。公式I的化合物表现为血小板活化因子（PAF）拮抗剂的活性，因此，在由于过量血小板活化因子而表现出的疾病状态中或用于预防和治疗心血管疾病、肺部疾病、免疫性疾病、炎症性疾病、皮肤病、休克或移植排斥时，这些化合物是有用的。
• ５，５−ジアリール−２，４−ペンタジエン酸エステル系化合物および該化合物を有効成分とする紫外線吸収剤
  申请人：——

  公开号：JP2002053527A

  公开（公告）日：2002-02-19

  (57)【要約】\n【課題】 紫外線、特に長波長側紫外線ＵＶ−Ａに対し高い吸収能を有する化合物、該化合物を有効成分とする紫外線吸収剤、及び該紫外線吸収剤を含有する皮膚外用剤の提供。\n【解決手段】 下記一般式(Ｉａ）；\n【化１４】\n（式中、Ｒ1、Ｒ2、Ｒ3及び4は水素、Ｃ1〜4のアルキル基、アルコキシ基、ハロゲン原子であるか或いは隣接する炭素原子上のＲ1とＲ2又はＲ3とＲ4が一緒になってメチレンジオキシ基を形成しており、Ｒ5はＣ1〜18のアルキル基又はアルケニル基であり、Ｒ1、Ｒ2、Ｒ3及びＲ4のすべてが水素のときはＲ5はＣ2〜18のアルキル基又は分岐状のアルケニル基である。）で表される５，５−ジアリール−２，４−ペンタジエン酸エステル系化合物、前記化合物及び５，５−ジフェニル−２，４−ペンタジエン酸メチルの１種以上を有効成分とする紫外線吸収剤、並びに該紫外線吸収剤を含有する皮膚外用剤。

  (57) [摘要] Јn[主题事项] 提供一种对紫外线，特别是长波长侧紫外线UV-A具有高吸收能力的化合物，一种包含所述化合物作为活性成分的紫外线吸收剂，以及一种含有所述紫外线吸收剂的局部皮肤涂抹剂。\以下通式（Ia）；Јn [Ј14]Јn（其中 R1、R2、R3 和 4 是氢、C1-4 烷基、烷氧基、卤素原子或相邻碳原子上的 R1 和 R2 或 R3 和 R4 一起形成亚甲基二氧基，R5 是 C1 至当 R1、R2、R3 和 R4 均为氢时，R5 为 C2-18 烷基或支链烯基）。以上述化合物和 5,5-二苯基-2,4-戊二烯酸酯为代表的 5,5-二芳基-2,4-戊二烯酸酯化合物。包含一种或多种上述化合物和 5,5-二苯基-2,4-戊二烯酸甲酯作为活性成分的紫外线吸收剂，以及含有该紫外线吸收剂的局部皮肤应用。
• GUTHRIE, ROBERT W.;KAPLAN, GERALD L.;MENNONA, FRANCIS A.;TILLEY, JEFFERSO+, J. MED. CHEM., 32,(1989) N, C. 1820-1835
  作者：GUTHRIE, ROBERT W.、KAPLAN, GERALD L.、MENNONA, FRANCIS A.、TILLEY, JEFFERSO+

  DOI：——

  日期：——
• US4788206A
  申请人：——

  公开号：US4788206A

  公开（公告）日：1988-11-29
• US4975438A
  申请人：——

  公开号：US4975438A

  公开（公告）日：1990-12-04