(5Z, 13E)-(9α,11α,15R)-9-acetoxy-11-(tetrahydropyran-2-yloxy)-15-hydroxy-16-(4-chlorophenoxy)-17,18,19,20-tetranorprosta-5,13-dienoic acid methyl ester | 62525-18-2

• 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: (5Z, 13E)-(9α,11α,15R)-9-acetoxy-11-(tetrahydropyran-2-yloxy)-15-hydroxy-16-(4-chlorophenoxy)-17,18,19,20-tetranorprosta-5,13-dienoic acid methyl ester
• 英文别名: methyl (Z)-7-[(1R,2R,3R,5S)-5-acetyloxy-2-[(E,3R)-4-(4-chlorophenoxy)-3-hydroxybut-1-enyl]-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate
• CAS: 62525-18-2
• 化学式: C₃₀H₄₁ClO₈
• 分子量: 565.104
• InChiKey: NUMBBAPFOBLGAJ-QEEKERJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5Z, 13E)-(9α,11α,15R)-9-acetoxy-11-(tetrahydropyran-2-yloxy)-15-hydroxy-16-(4-chlorophenoxy)-17,18,19,20-tetranorprosta-5,13-dienoic acid methyl ester 在 potassium carbonate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.66h， 生成 (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(4-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester
  参考文献：
  名称：

  Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain

  摘要：

  Additional double bonds were introduced into the alpha chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16-[3-(tri-fluoromethyl)phenoxy]-, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects. Of these analogues, the delta 3-cis-delta 5 analogues 23b is 1200 times more potent than prostaglandin F2 alpha in antinidatory effect in the rat and more potent than any other known prostaglandin analogues.

  DOI：

  10.1021/jm00179a011
• 作为产物：
  描述：

  methyl (Z)-7-((1R,2S,3R,5S)-5-acetoxy-2-(((2-methoxypropan-2-yl)oxy)methyl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate 在 盐酸 、 sodium tetrahydroborate 、 pyridine-SO3 complex 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 5.08h， 生成 (5Z, 13E)-(9α,11α,15R)-9-acetoxy-11-(tetrahydropyran-2-yloxy)-15-hydroxy-16-(4-chlorophenoxy)-17,18,19,20-tetranorprosta-5,13-dienoic acid methyl ester
  参考文献：
  名称：

  Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain

  摘要：

  Additional double bonds were introduced into the alpha chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16-[3-(tri-fluoromethyl)phenoxy]-, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects. Of these analogues, the delta 3-cis-delta 5 analogues 23b is 1200 times more potent than prostaglandin F2 alpha in antinidatory effect in the rat and more potent than any other known prostaglandin analogues.

  DOI：

  10.1021/jm00179a011

文献信息

• Prostacyclin analogues
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US04367237A1

  公开（公告）日：1983-01-04

  Prostaglandin analogues of the general formula: ##STR1## [wherein the ring A represents: ##STR2## the ring B represents: ##STR3## (wherein R.sup.6 represents hydrogen, methyl or ethyl, and r is zero, one or two), Y represents ethylene, cis- or trans-vinylene or ethynylene, Z represents a grouping of the formula: --(CH.sub.2).sub.m --, --(CH.sub.2).sub.3 --CHR.sup.7 --, --(CH.sub.2).sub.2 --CHR.sup.7 --CH.sub.2 --, --CH.sub.2 --CHR.sup.7 --(CH.sub.2).sub.2 --, --CHR.sup.7 --(CH.sub.2).sub.3 --, or trans--(CH.sub.2).sub.2 --CH.dbd.CH-- (wherein m is 3, 4 or 5, and R.sup.7 represents methyl or ethyl), R.sup.1 represents a grouping of the formula: --COOR.sup.8, ##STR4## or --CH.sub.2 OR.sup.11 (wherein R.sup.8 represents hydrogen, alkyl, aralkyl, cycloalkyl which is unsubstituted or substituted by at least one alkyl group, or R.sup.8 represents phenyl which is unsubstituted or substituted by halogen, trifluoromethyl, alkyl, alkoxy, alkylthio or phenyl, or represents naphthyl, 2,3- or 1,3-dihydroxypropyl, 2,3- or 1,3-bisalkanoyloxypropyl, a grouping of the formula: -D.sub.1 --COOR.sup.12, ##STR5## -D.sub.2 -R.sup.15 or -D.sub.3 -R.sup.16, wherein D.sub.1 represents alkylene, D.sub.2 represents alkylene, D.sub.3 represents a single bond or alkylene, R.sup.12, R.sup.13 and R.sup.14, each represent alkyl, R.sup.15 represents hydroxy, alkoxy or alkylthio and R.sup.16 represents a heterocyclic ring, or R.sup.8 represents a grouping of the formula: ##STR6## R.sup.9 and R.sup.10, each represent hydrogen, alkyl, alkylsulphonyl, alkanoyl or ##STR7## represents a heterocyclic ring, and R.sup.11 represents hydrogen or alkanoyl, R.sup.2 represents hydrogen, methyl or ethyl, R.sup.3 represents a single bond or alkylene, R.sup.4 represents hydrogen, alkyl, alkoxy, cycloalkyl or cycloalkyloxy unsubstituted or substituted by alkyl, or represents phenyl or phenoxy unsubstituted or substituted by halogen, trifluoromethyl or alkyl with the proviso that, when R.sup.3 represents a single bond, R.sup.4 does not represent alkoxy, cycloalkyloxy or phenoxy, R.sup.5 represents hydrogen, methyl or ethyl and with the proviso that, when one of the groups R.sup.5, R.sup.6 and R.sup.7 represents methyl or ethyl the other two groups are hydrogen atoms] and cyclodextrin clathrates, non-toxic salts and non-toxic acid addition salts thereof, possess selective strong stimulatory activity on uterine contraction in female mammals.

  通式为：##STR1##的前列腺素类似物 [其中环A表示：##STR2##环B表示：##STR3##（其中R.sup.6表示氢，甲基或乙基，r为零，一或二），Y表示乙烯，顺式或反式乙烯基或乙炔基，Z表示以下式的基团：--(CH.sub.2).sub.m --，--(CH.sub.2).sub.3 --CHR.sup.7 --，--(CH.sub.2).sub.2 --CHR.sup.7 --CH.sub.2 --，--CH.sub.2 --CHR.sup.7 --(CH.sub.2).sub.2 --，--CHR.sup.7 --(CH.sub.2).sub.3 --或反- --(CH.sub.2).sub.2 --CH.dbd.CH--（其中m为3、4或5，R.sup.7表示甲基或乙基），R.sup.1表示以下式的基团：--COOR.sup.8，##STR4##或--CH.sub.2 OR.sup.11（其中R.sup.8表示氢，烷基，芳基烷基，环烷基，未取代或被至少一个烷基取代，或R.sup.8表示未取代或被卤素，三氟甲基，烷基，烷氧基，烷硫基或苯基取代的苯基，或表示萘基，2,3-或1,3-二羟基丙基，2,3-或1,3-双烷酰氧基丙基，以下式的基团：-D.sub.1 --COOR.sup.12，##STR5##-D.sub.2 -R.sup.15或-D.sub.3 -R.sup.16，其中D.sub.1表示烷基，D.sub.2表示烷基，D.sub.3表示单键或烷基，R.sup.12、R.sup.13和R.sup.14分别表示烷基，R.sup.15表示羟基，烷氧基或烷硫基，R.sup.16表示杂环环，或R.sup.8表示以下式的基团：##STR6##R.sup.9和R.sup.10，分别表示氢，烷基，烷基磺酰，烷酰或##STR7##表示杂环环，R.sup.11表示氢或烷酰，R.sup.2表示氢，甲基或乙基，R.sup.3表示单键或烷基，R.sup.4表示氢，烷基，烷氧基，环烷基或未取代或被烷基取代的环烷氧基，或表示未取代或被卤素，三氟甲基或烷基取代的苯基或苯氧基，但当R.sup.3表示单键时，R.sup.4不表示烷氧基，环烷氧基或苯氧基，R.sup.5表示氢，甲基或乙基，但当其中一个基团R.sup.5，R.sup.6和R.sup.7表示甲基或乙基时，另外两个基团为氢原子]和环糊精包合物，其非毒性盐和非毒性酸加合盐，在雌性哺乳动物子宫收缩方面具有选择性强烈的刺激活性。
• Trans-.DELTA..sup.2 -pge alkylsulphonyl amides
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US04390548A1

  公开（公告）日：1983-06-28

  Prostaglandin analogues of the formula: ##STR1## (wherein R.sup.1 represents an alkyl group containing from 1 to 4 carbon atoms, R.sup.2 represents a single bond or an alkylene group containing from 1 to 5 carbon atoms, R.sup.3 represents a hydrogen atom, an alkyl or alkoxy group containing from 1 to 8 carbon atoms, a cycloalkyl or cycloalkyloxy group containing from 4 to 7 carbon atoms and being unsubstituted or substituted by at least one alkyl group containing from 1 to 8 carbon atoms, or a phenyl or phenoxy group unsubstituted or substituted by at least one halogen atom, trifluoromethyl group or alkyl group containing from 1 to 4 carbon atoms, R.sup.4 represents a hydrogen atom or a hydroxy-protecting group which may be removed under acidic conditions, X represents an ethylene group or a cis-vinylene group, the double bonds between the carbon atoms in positions 2 and 3 and between the carbon atoms in positions 13 and 14 are both in trans-configuration, and the wavy line attached to the carbon atom in position 15 represents .alpha.- or .beta.-configuration or a mixture thereof, provided that, when R.sup.2 represents a single bond, R.sup.3 does not represent an alkoxy group, a cycloalkoxy group or a phenoxy group) and cyclodextrin clathrates thereof are useful compounds: those in which R.sup.4 represents a hydrogen atom possess selective prostaglandin-like properties.

  公式为：##STR1##的前列腺素类似物（其中R.sup.1代表含有1至4个碳原子的烷基，R.sup.2代表单键或含有1至5个碳原子的亚烷基，R.sup.3代表氢原子，含有1至8个碳原子的烷基或烷氧基，含有4至7个碳原子的环烷基或环烷氧基，未取代或被至少一个含有1至8个碳原子的烷基取代，或未取代或被至少一个卤素原子、三氟甲基基团或含有1至4个碳原子的烷基取代的苯基或苯氧基，R.sup.4代表氢原子或在酸性条件下可去除的羟基保护基，X代表乙烯基或顺式-乙烯基，位于2和3号碳原子之间以及13和14号碳原子之间的双键均为反式构型，附加在15号碳原子上的波浪线代表.alpha.-或.beta.-构型或其混合物，但当R.sup.2代表单键时，R.sup.3不代表烷氧基，环烷氧基或苯氧基），以及其环糊精包合物是有用的化合物：其中R.sup.4代表氢原子的化合物具有选择性类前列腺素的特性。
• US4367237A
  申请人：——

  公开号：US4367237A

  公开（公告）日：1983-01-04