PGF_2α methyl ester 11,15-bis(tetrahydropyranyl ether) | 55955-05-0

• 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: PGF_2α methyl ester 11,15-bis(tetrahydropyranyl ether)
• 英文别名: (5Z,13E)-(9α,11α,15S)-9-hydroxy-11,15-bis-(tetrahydropyran-2-yloxy)prosta-5,13-dienoic acid methyl ester；(5Z,13E)-(9α,11α,15S)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-5,13-dienoic acid methyl ester；PGE 2α-methylester-11,15-bis(tetrahydropyranylether)；(5Z,13E)-(9alpha,11alpha,15S)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-5,13-dienoic acid methyl ester；methyl (Z)-7-[(1R,2R,3R,5S)-5-hydroxy-3-(oxan-2-yloxy)-2-[(E,3S)-3-(oxan-2-yloxy)oct-1-enyl]cyclopentyl]hept-5-enoate
• CAS: 55955-05-0
• 化学式: C₃₁H₅₂O₇
• 分子量: 536.75
• InChiKey: GXVGCKZJZILLQE-IQGKLULKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  PGF_2α methyl ester 11,15-bis(tetrahydropyranyl ether) 在 4-二甲氨基吡啶 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 2.4h， 生成 (Z)-7-[(1r,2r,3r,5s)-5-乙酰氧基-3-羟基-2-((e)-(s)-3-羟基-1-辛烯)-环戊基]-5-庚烯酸甲酯
  参考文献：
  名称：

  Synthesis of (5E)- and (5Z)-11-deoxy-6,11.alpha.-epoxy-.DELTA.5-prostaglandin F1.alpha. sodium salts: 6,11.alpha.-enol ether isomers of prostacyclin

  摘要：

  DOI：

  10.1021/jo00146a019

文献信息

• Prostaglandin 12 analogues and their pharmaceutical compositions
  申请人：Ono Pharmaceutical Co. Ltd.

  公开号：US04399147A1

  公开（公告）日：1983-08-16

  Prostaglandin I.sub.2 analogues of the formula: ##STR1## [wherein X represents trans-vinylene or an ethylene group unsubstituted or substituted by a bromine atom at the C-5 position, Y represents trans-vinylene or ethylene, R.sup.1 represents hydrogen or an alkyl group containing from 1 to 12 carbon atoms, R.sup.2 represents hydrogen or methyl or ethyl, R.sup.3 represents a single bond or an alkylene group containing from 1 to 4 carbon atoms, R.sup.4 represents hydrogen, an alkyl group containing from 1 to 8 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group containing from 1 to 8 carbon atoms, or a phenyl or phenoxy group unsubstituted or carrying at least one substituent selected from halogen atoms, the trifluoromethyl group and alkyl groups containing from 1 to 3 carbon atoms, and the wavy line attached to the carbon atoms in positions 6, 11 and 15 depicted in the formula represents .alpha.- or .beta.-configuration or mixtures thereof] are new compounds possessing pharmacological properties typical of prostaglandins, for example PGI.sub.2, and are more stable than PGI.sub.2.

  公式为：##STR1##的前列腺素I.sub.2类似物[其中X代表反式乙烯基或未取代或取代在C-5位置的溴原子的乙烯基，Y代表反式乙烯基或乙烯基，R.sup.1代表氢或含有1至12个碳原子的烷基，R.sup.2代表氢或甲基或乙基，R.sup.3代表单键或含有1至4个碳原子的烷基，R.sup.4代表氢，含有1至8个碳原子的烷基，含有4至7个碳原子的环烷基，未取代或取代至少一个含有1至8个碳原子的烷基的苯基或苯氧基，或未取代或携带至少一个取自卤原子、三氟甲基基团和含有1至3个碳原子的烷基的取代基，图式中连接到6、11和15位置的碳原子上的波浪线代表α-或β-构型或其混合物]是具有类似于前列腺素，例如PGI.sub.2的药理特性的新化合物，并且比PGI.sub.2更稳定。
• Prostaglandin analogues
  申请人：Ono Pharmaceutical Co. Ltd.

  公开号：US04215142A1

  公开（公告）日：1980-07-29

  Prostaglandin E.sub.1 analogues of the general formula: ##STR1## [wherein Y represents ethylene or trans-vinylene, Z represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom, an alkyl group containing from 1 to 12 carbon atoms, an aralkyl group containing from 7 to 12 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group containing from 1 to 6 carbon atoms, a phenyl group unsubstituted or substituted by at least one chlorine atom, trifluoromethyl group, alkyl group containing from 1 to 4 carbon atoms or phenyl group, a --C.sub.m H.sub.2m COOR.sup.5 group (wherein m represents an integer of from 1 to 12 and R.sup.5 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.6 group (wherein R.sup.6 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and n represents an integer of from 2 to 12), or a ##STR2## group (wherein R.sup.7 and R.sup.8 each represent a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and n is as hereinbefore defined), R.sup.2 represents a hydrogen atom or a methyl or ethyl group, R.sup.3 represents a single bond or an alkylene group containing from 1 to 4 carbon atoms, R.sup.4 represents a hydrogen atom, an alkyl group containing from 1 to 8 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group containing from 1 to 8 carbon atoms, or represents a phenyl or phenoxy group unsubstituted or substituted by at least one chlorine atom, trifluoromethyl group or alkyl group containing from 1 to 3 carbon atoms, and the wavy line attached to the C-11 and C-15 carbon atoms represents .alpha.- or .beta.- configuration or mixtures thereof] and cyclodextrin clathrates thereof, and, when R.sup.1 represents a hydrogen atom or a group C.sub.m H.sub.2m COOR.sup.5 in which R.sup.5 represents a hydrogen atom, non-toxic salts thereof and, when R.sup.1 represents a group ##STR3## non-toxic acid addition salts thereof, are new compounds and possess characteristic prostaglandin-like properties.

  通式为：##STR1##[其中，Y代表乙烯或顺式乙烯基，Z代表乙烯或顺式乙烯基，R.sup.1代表氢原子，含有1到12个碳原子的烷基，含有7到12个碳原子的芳基烷基，含有4到7个碳原子的环烷基，未取代或取代至少一个含有1到6个碳原子的烷基，未取代或取代至少一个氯原子、三氟甲基基团、含有1到4个碳原子的烷基或苯基的苯基，--C.sub.m H.sub.2m COOR.sup.5基团（其中m表示1到12的整数，R.sup.5表示氢原子或含有1到4个碳原子的烷基），--C.sub.n H.sub.2n OR.sup.6基团（其中R.sup.6表示氢原子或含有1到4个碳原子的烷基，n表示2到12的整数），或者##STR2##基团（其中R.sup.7和R.sup.8各自代表氢原子或含有1到4个碳原子的烷基，n如上所述），R.sup.2代表氢原子或甲基或乙基基团，R.sup.3代表单键或含有1到4个碳原子的烷基，R.sup.4代表氢原子，含有1到8个碳原子的烷基，含有4到7个碳原子的环烷基，未取代或取代至少一个含有1到8个碳原子的烷基，或者代表未取代或取代至少一个氯原子、三氟甲基基团或含有1到3个碳原子的烷基的苯基或苯氧基，连接到C-11和C-15碳原子的波浪线表示α-或β-构型或其混合物]及其环糊精包合物，当R.sup.1代表氢原子或C.sub.m H.sub.2m COOR.sup.5基团（其中R.sup.5代表氢原子）时，其非毒性盐，当R.sup.1代表##STR3##基团时，其非毒性酸加盐物是新的化合物，具有特征性的前列腺素样性质。
• US4215142A
  申请人：——

  公开号：US4215142A

  公开（公告）日：1980-07-29
• US4278688A
  申请人：——

  公开号：US4278688A

  公开（公告）日：1981-07-14
• US4399147A
  申请人：——

  公开号：US4399147A

  公开（公告）日：1983-08-16