2-bromo-1-methylethylphosphoric acid 3-(hexadecyloxy)-2-(phenylmethoxy)propyl ester | 118469-66-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 2-bromo-1-methylethylphosphoric acid 3-(hexadecyloxy)-2-(phenylmethoxy)propyl ester
• 英文别名: 1-Bromopropan-2-yl (3-hexadecoxy-2-phenylmethoxypropyl) hydrogen phosphate
• CAS: 118469-66-2
• 化学式: C₂₉H₅₂BrO₆P
• 分子量: 607.606
• InChiKey: XGBVXGGJRRKHJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  37
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-bromo-1-methylethylphosphoric acid 3-(hexadecyloxy)-2-(phenylmethoxy)propyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 40.0h， 生成 (2-Acetyloxy-3-hexadecoxypropyl) 1-(trimethylazaniumyl)propan-2-yl phosphate
  参考文献：
  名称：

  Analogs of platelet activating factor. 4. Some modifications of the phosphocholine moiety

  摘要：

  Racemic analogues of platelet activating factor (PAF) in which the methylene bridge separating the phosphate and trimethylammonium moieties is altered in length (7a-f) have been prepared. Increasing the length of this bridge results in a progressive decrease in the hypotensive and platelet aggregation responses. Analogues in which the phosphocholine group is substituted with a methyl group (7h and 7i) or a phenyl group (5j) or in which the methylene bridge is replaced with a meta-substituted benzyl group (5k) have been prepared. With respect to both the blood pressure and platelet aggregation responses, 7i and 5k showed little if any changes in potency compared to racemic C16-PAF (1a). While 7h is more potent than 1a with respect to both the hypotensive and platelet aggregation properties, 5j is less potent. Replacement of the phosphate moiety of C18-PAF (1b) with a phosphonate group (7g) leads to decreased activity in both assays. Analogue 11, in which the phosphocholine group has been replaced with a 4-(trimethylammonio)butoxy group, exhibited no detectable hypotensive or platelet aggregating activity. None of the analogues exhibited a separation of the blood pressure and platelet aggregation activities.

  DOI：

  10.1021/jm00153a005
• 作为产物：
  描述：

  [1-[1-bromopropan-2-yloxy(chloro)phosphoryl]oxy-3-hexadecoxypropan-2-yl]oxymethylbenzene 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2-bromo-1-methylethylphosphoric acid 3-(hexadecyloxy)-2-(phenylmethoxy)propyl ester
  参考文献：
  名称：

  Analogs of platelet activating factor. 4. Some modifications of the phosphocholine moiety

  摘要：

  Racemic analogues of platelet activating factor (PAF) in which the methylene bridge separating the phosphate and trimethylammonium moieties is altered in length (7a-f) have been prepared. Increasing the length of this bridge results in a progressive decrease in the hypotensive and platelet aggregation responses. Analogues in which the phosphocholine group is substituted with a methyl group (7h and 7i) or a phenyl group (5j) or in which the methylene bridge is replaced with a meta-substituted benzyl group (5k) have been prepared. With respect to both the blood pressure and platelet aggregation responses, 7i and 5k showed little if any changes in potency compared to racemic C16-PAF (1a). While 7h is more potent than 1a with respect to both the hypotensive and platelet aggregation properties, 5j is less potent. Replacement of the phosphate moiety of C18-PAF (1b) with a phosphonate group (7g) leads to decreased activity in both assays. Analogue 11, in which the phosphocholine group has been replaced with a 4-(trimethylammonio)butoxy group, exhibited no detectable hypotensive or platelet aggregating activity. None of the analogues exhibited a separation of the blood pressure and platelet aggregation activities.

  DOI：

  10.1021/jm00153a005

文献信息

• Sulfur inhibitors of phospholipase A-Z
  申请人：American Cyanamid Company

  公开号：US05126291A1

  公开（公告）日：1992-06-30

  Phospholipase A.sub.2 inhibitors having the formula ##STR1## wherein R" is a C.sub.2 -C.sub.20 alkyl group, R.sub.1 " is a C.sub.1 -C.sub.4 alkyl group, y is an integer from 2 to 10, and J.sup.- is a pharmaceutically acceptable anion, are described.

  描述具有以下结构的磷脂酶A.sub.2抑制剂##STR1##其中R"是C.sub.2-C.sub.20烷基基团，R.sub.1 "是C.sub.1-C.sub.4烷基基团，y是2到10之间的整数，J.sup.-是一种药用可接受的阴离子。
• Antihypertensive phosphate derivatives
  申请人：American Cyanamid Co.

  公开号：US04762942A1

  公开（公告）日：1988-08-09

  Antihypertensive phosphate derivatives having the following formula are described: ##STR1## wherein X is selected from one or more of: (a) C.sub.1 -C.sub.24 branched or straight chain alkyl; (b) C.sub.1 -C.sub.24 branched or straight chain alkoxy; (c) ##STR2## wherein n and m are integers from 0 to 25 and the sum of n and m is less than or equal to 25; phenyl; substituted phenyl wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, C.sub.1 -C.sub.20 branched or straight chain alkoxy, halogen, trifluoromethyl, phenyl, and substituted phenyl, phenoxy; and substituted phenoxy, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, halogen, trifluoromethyl, phenyl and substituted phenyl; Q is selected from the group consisting of: ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.4 branched or straight chain alkoxy and C.sub.1 -C.sub.4 branched or straight chain alkylamino and wherein R.sub.3 is C.sub.1 -C.sub.4 alkyl, with the proviso that when Q is ##STR4## then R.sub.1 is C.sub.1 -C.sub.4 branched or straight chain alkyl; T is a bivalent radical selected from the group consisting of --(CHR).sub.p -- and ##STR5## wherein p is an integer from 1 to 15, the moiety --(CHR).sub.p -- represents an alkylene chain substituted at any position with one or more C.sub.1 -C.sub.10 alkyl groups or phenyl groups, and the moiety ##STR6## is bound with the oxygen atom attached directly to the aromatic ring; and Z is ##STR7## wherein R.sub.2 is hydrogen or C.sub.1 -C.sub.4 branched or straight chain alkyl and q is an interger from 4 to 7; in either the racemic or optically active forms.

  描述具有以下公式的抗高血压磷酸盐衍生物：##STR1##其中X从以下一个或多个中选择：(a) C.sub.1 -C.sub.24支链或直链烷基；(b) C.sub.1 -C.sub.24支链或直链烷氧基；(c) ##STR2##其中n和m是从0到25的整数，n和m的和小于或等于25；苯基；取代苯基，其中取代基选择自C.sub.1 -C.sub.20支链或直链烷基、C.sub.1 -C.sub.20支链或直链烷氧基、卤素、三氟甲基、苯基和取代苯基、苯氧基；和取代苯氧基，其中取代基选择自C.sub.1 -C.sub.20支链或直链烷基、卤素、三氟甲基、苯基和取代苯基；Q从以下一组中选择：##STR3##其中R.sub.1选择自氢、C.sub.1 -C.sub.4支链或直链烷基、C.sub.1 -C.sub.4支链或直链烷氧基和C.sub.1 -C.sub.4支链或直链烷基氨基，其中R.sub.3是C.sub.1 -C.sub.4烷基，但要注意当Q为##STR4##时，R.sub.1为C.sub.1 -C.sub.4支链或直链烷基；T是从--(CHR).sub.p --和##STR5##中选择的二价基团，其中p是从1到15的整数，基团--(CHR).sub.p --代表一个在任何位置上用一个或多个C.sub.1 -C.sub.10烷基或苯基取代的烷基链，基团##STR6##与直接连接到芳香环的氧原子结合；Z是##STR7##其中R.sub.2是氢或C.sub.1 -C.sub.4支链或直链烷基，q是从4到7的整数；可以是消旋的或光学活性形式。
• WISSNER, ALLAN;SUM, PHAIK E.;SCHAUB, ROBERT E.
  作者：WISSNER, ALLAN、SUM, PHAIK E.、SCHAUB, ROBERT E.

  DOI：——

  日期：——
• US4762942A
  申请人：——

  公开号：US4762942A

  公开（公告）日：1988-08-09
• US4883816A
  申请人：——

  公开号：US4883816A

  公开（公告）日：1989-11-28