[1S-[1α,2β(5Z),3β,4α]]-7-[3-(hydroxymethyl)-7-oxabicyclo[ 2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester | 96444-21-2

• 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: [1S-[1α,2β(5Z),3β,4α]]-7-[3-(hydroxymethyl)-7-oxabicyclo[ 2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester
• 英文别名: [1α,2β(5Z),3β,4α]-7-[3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester；[1α,2β(Z),3β,4α]-7-[3-(hydroxymethyl)-7-oxabicyclo[2.2.1]-hept-2-yl]-5-heptenoic acid, methyl ester；[1α,2β(Z),3β,4α]-7-[3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester；methyl (Z)-7-[(1S,2S,3S,4R)-3-(hydroxymethyl)-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoate
• CAS: 96444-21-2
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: UPQBIDVBPDGLHJ-ULYOJFKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [1S-[1α,2β(5Z),3β,4α]]-7-[3-(hydroxymethyl)-7-oxabicyclo[ 2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester 在 吡啶 、 chromium(III) oxide 、 lithium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 16.62h， 生成 <1S-(1α,2α(5Z),3α(1E,3R*),4α)>-7-<3-(3-hydroxy-1-octenyl)-7-oxabicyclo<2.2.1>heptan-1-yl>-5-heptanoic acid
  参考文献：
  名称：

  血栓烷A2 / PGH2的7-氧杂双环[2.2.1]庚烷类似物的合成及体外药理作用。

  摘要：

  为了寻找有用的TXA2 / PGH2介导的病理生理抑制剂，制备了一系列以天然产物的结构为模型的化学稳定的TXA2 / PGH2类似物。以手性形式制备结构1所示的16种异构体，并评估其在血小板和平滑肌中的体外活性。根据相对的侧链和甲醇的立体化学，观察到TXA2 / PGH2激动剂和拮抗剂，以及令人惊讶的是PGD2 / PGI2激动剂活性。具有1所示的α杂环的对映体通常比其镜像异构体更有效。

  DOI：

  10.1021/jm00149a007
• 作为产物：
  描述：

  (1R,2S,7R,8S)-3,11-dioxatricyclo[6.2.1.02,7]undecan-5-ol 生成 [1S-[1α,2β(5Z),3β,4α]]-7-[3-(hydroxymethyl)-7-oxabicyclo[ 2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester
  参考文献：
  名称：

  HALL, S. E.;HASLANGER, M. F.

  摘要：

  DOI：

文献信息

• 7-oxabicycloheptane substituted hydroxamic acid prostaglandin analogs
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04734425A1

  公开（公告）日：1988-03-29

  7-Oxabicycloheptane substituted hydroxamic acid prostaglandin analogs are provided having the structural formula ##STR1## wherein A is --CH.dbd.CH-- or --CH.sub.2 -CH.sub.2 --; n is 1 to 5; R is CO.sub.2 H, CO.sub.2 alkyl, CO.sub.2 alkali metal, CO.sub.2 polyhydroxyamine salt, --CH.sub.2 OH, ##STR2## wherein R.sup.4 and R.sup.5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R.sup.4 and R.sup.5 being other than hydroxy and lower alkoxy; q is 1 to 12, R.sup.1 is H or OH; R.sup.2 is OH or H, provided that one of R.sup.1 and R.sup.2 is OH and the other is H; and R.sup.3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, ##STR3## (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.

  提供了7-Oxabicycloheptane取代羟肟酸前列腺素类似物，具有结构式##STR1##其中A为--CH.dbd.CH--或--CH.sub.2 -CH.sub.2--; n为1至5; R为CO.sub.2 H，CO.sub.2烷基，CO.sub.2碱金属，CO.sub.2多羟胺盐，--CH.sub.2 OH，##STR2##其中R.sup.4和R.sup.5相同或不同，为H，低碳烷基，羟基，低碳氧基或芳基，R.sup.4和R.sup.5中至少有一个不是羟基和低碳氧基; q为1至12，R.sup.1为H或OH; R.sup.2为OH或H，条件是R.sup.1和R.sup.2中的一个为OH，另一个为H; R.sup.3为H，低碳烷基，低碳烯基，低碳炔基，芳基，芳基烷基，低碳氧基，芳氧基，芳基烷氧基，氨基，烷基氨基芳基氨基，芳基烷基氨基，##STR3##（其中n'为0、1或2），烷基氨基烷基，芳基氨基烷基，芳基烷基氨基烷基，烷氧基烷基，芳氧基烷基或芳基烷氧基。这些化合物是心血管药物，例如，在治疗血栓性疾病方面有用。
• 7-Oxabicycloheptane substituted enaminone prostaglandin analogs and
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04533673A1

  公开（公告）日：1985-08-06

  7-Oxabicycloheptane substituted enaminone prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.

  提供了具有结构式##STR1##的7-氧杂双环庚烷取代烯胺酮前列腺素类似物，包括其所有立体异构体。这些化合物是心血管药物，例如，在溶栓疾病治疗中有用。
• 7-Oxabicycloheptane substituted prostaglandin alcohols and their use in
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04542156A1

  公开（公告）日：1985-09-17

  7-Oxabicycloheptane substituted prostaglandin alcohols are provided having the structural formula ##STR1## wherein A is --CH.dbd.CH--(CH.sub.2).sub.n -- or (CH.sub.2).sub.q ; B is a single bond or --CH.dbd.CH--; n is 1 to 5; q is 1 to 6; Q is --CH.dbd.CH-- or (CH.sub.2).sub.2 ; and R is lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl or lower alkenyl, with the proviso that when B is --CH.dbd.CH--, n is 1 to 3 or q is 1 to 4 and when B is a single bond, n is 1 to 5 or q is 1 to 6, and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.

  提供了具有结构式的7-氧杂双环庚烷取代前列腺素醇##STR1##其中A是--CH.dbd.CH--(CH.sub.2).sub.n--或(CH.sub.2).sub.q; B是单键或--CH.dbd.CH--; n为1至5; q为1至6; Q为--CH.dbd.CH--或(CH.sub.2).sub.2; R为低碳基、芳基、芳基烷基、环烷基、环烷基烷基或低烯基，但是当B是--CH.dbd.CH--时，n为1至3或q为1至4，当B是单键时，n为1至5或q为1至6，并包括所有立体异构体。这些化合物是心血管药物，例如，在治疗溶栓性疾病方面有用。
• 7-oxabicycloheptane substituted prostaglandin compounds useful in the
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04626548A1

  公开（公告）日：1986-12-02

  7-Oxabicycloheptane substituted prostaglandin alcohols are provided having the structural formula ##STR1## wherein A is --CH.dbd.CH-- or (CH.sub.2).sub.2 ; m is 1 to 5; Q is --CH.dbd.CH-- or (CH.sub.2).sub.2 ; R is H, alkali metal or alkyl; and R.sup.2 is ##STR2## wherein R.sup.3 is H or lower alkyl and R.sup.4 is H or I and including all steroisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.

  提供了具有结构式的7-Oxabicycloheptane取代前列腺素醇##STR1##其中A为--CH.dbd.CH--或(CH.sub.2).sub.2; m为1至5; Q为--CH.dbd.CH--或(CH.sub.2).sub.2; R为H、碱金属或烷基; R.sup.2为##STR2##其中R.sup.3为H或较低烷基，R.sup.4为H或I，包括所有立体异构体。这些化合物是心血管药物，例如，可用于治疗血栓性疾病。
• 7-Oxabicycloheptane substituted oxa prostaglandin analogs and their use
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04542157A1

  公开（公告）日：1985-09-17

  7-Oxabicycloheptane substituted oxo prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl, alkali metal or tris(hydroxymethyl)aminomethane, R.sup.1 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl or cycloalkylalkyl, A is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --, y is 0 to 4, m is 0 to 8, and n is 1 to 4, p is 1 to 12 and q is 0 to 5, and including all stereoisomers thereof. The compounds are antiinflammatory agents useful, for example, in the treatment of inflammatory diseases and analgesic agents as well as cardiovascular agents useful, for example, in the treatment of thrombolytic disease.

  提供了结构式为##STR1##的7-Oxabicycloheptane取代氧代前列腺素类似物，其中R为氢、较低烷基、碱金属或三(羟甲基)胺甲烷，R.sup.1为氢、较低烷基、芳基、芳基烷基、环烷基或环烷基烷基，A为--CH.dbd.CH--或--(CH.sub.2).sub.2 --，y为0至4，m为0至8，n为1至4，p为1至12，q为0至5，并包括所有立体异构体。这些化合物是抗炎药物，例如，在治疗炎症性疾病和镇痛药物方面有用，同时也是心血管药物，例如，在治疗溶栓性疾病方面有用。