2-methylene-3-<<(octadecylamino)carbonyl>oxy>propyl 7-bromoheptanoate | 111879-49-3

• 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: 2-methylene-3-<<(octadecylamino)carbonyl>oxy>propyl 7-bromoheptanoate
• 英文别名: 1-octadecylaminocarbonyloxy-3-(7-bromoheptanoyloxy)-2-methylenepropane；2-methylene-3-{[(octadecylamino)carbonyl]oxy}propyl 7-bromoheptanoate；2-(Octadecylcarbamoyloxymethyl)prop-2-enyl 7-bromoheptanoate
• CAS: 111879-49-3
• 化学式: C₃₀H₅₆BrNO₄
• 分子量: 574.683
• InChiKey: XWFMXQLQNAKMFK-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C(Solv: methanol (67-56-1))
• 沸点：
  624.4±55.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  36
• 可旋转键数：
  29
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  噻唑 、 2-methylene-3-<<(octadecylamino)carbonyl>oxy>propyl 7-bromoheptanoate 反应 7.0h， 以90%的产率得到3-{6-[(2-methylene-3-{[(octadecylamino)carbonyl]oxy}propoxy)carbonyl]hexyl}thiazolium bromide
  参考文献：
  名称：

  Derivatives of 2-methylenepropane-1,3-diol as new antagonists of platelet activating factor

  摘要：

  Two new achiral platelet activating factor (PAF) antagonists, N-[5-[[2-methylene-3- [[(octadecylamino)carbonyl]oxy]propoxy]carbonyl]pentyl]pyridinium bromide and 3-[6-[[2-methylene-3- [[(octadecylamino)carbonyl]oxy]propoxy]carbonyl]hexyl]thiazolium bromide were synthesized from 2-methylenepropane-1,3-diol. Platelet aggregation in platelet-rich plasma from rabbits, induced by racemic C16-PAF, was competitively antagonized by 9 or 10. At concentrations less than or equal to 10(-4) M, neither compound 9 nor compound 10 caused platelet aggregation, nor did they inhibit platelet aggregation induced by collagen or adenosine diphosphate. Bronchoconstriction in the guinea pig and hypotension in the rat, induced by racemic C16-PAF, were also effectively antagonized by 9 and 10. Both appear to be more potent as PAF antagonists than Takeda's CV-3988.

  DOI：

  10.1021/jm00401a017
• 作为产物：
  描述：

  异氰酸十八酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 2-methylene-3-<<(octadecylamino)carbonyl>oxy>propyl 7-bromoheptanoate
  参考文献：
  名称：

  Derivatives of 2-methylenepropane-1,3-diol as new antagonists of platelet activating factor

  摘要：

  Two new achiral platelet activating factor (PAF) antagonists, N-[5-[[2-methylene-3- [[(octadecylamino)carbonyl]oxy]propoxy]carbonyl]pentyl]pyridinium bromide and 3-[6-[[2-methylene-3- [[(octadecylamino)carbonyl]oxy]propoxy]carbonyl]hexyl]thiazolium bromide were synthesized from 2-methylenepropane-1,3-diol. Platelet aggregation in platelet-rich plasma from rabbits, induced by racemic C16-PAF, was competitively antagonized by 9 or 10. At concentrations less than or equal to 10(-4) M, neither compound 9 nor compound 10 caused platelet aggregation, nor did they inhibit platelet aggregation induced by collagen or adenosine diphosphate. Bronchoconstriction in the guinea pig and hypotension in the rat, induced by racemic C16-PAF, were also effectively antagonized by 9 and 10. Both appear to be more potent as PAF antagonists than Takeda's CV-3988.

  DOI：

  10.1021/jm00401a017

文献信息

• PROPANE-1,3-DIOL DERIVATIVES, A METHOD FOR THEIR PRODUCTION AND A PHARMACEUTICAL COMPOSITION
  申请人：LEO PHARMACEUTICAL PRODUCTS LTD. A/S (LOVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB)

  公开号：EP0247201B1

  公开（公告）日：1991-05-15
• GRUE-SZHUSTORENSEN, GUNNAR;NIELSEN, INGER MANN;NIELSEN, CHRISTIAN KAERGAA+, J. MED. CHEM., 31,(1988) N 6, 1174-1178
  作者：GRUE-SZHUSTORENSEN, GUNNAR、NIELSEN, INGER MANN、NIELSEN, CHRISTIAN KAERGAA+

  DOI：——

  日期：——
• US4945098A
  申请人：——

  公开号：US4945098A

  公开（公告）日：1990-07-31
• [EN] PROPANE-1,3-DIOL DERIVATIVES, A METHOD FOR THEIR PRODUCTION AND A PHARMACEUTICAL COMPOSITION
  申请人：LEO PHARMACEUTICAL PRODUCTS LTD. A/S

  公开号：WO1987003281A1

  公开（公告）日：1987-06-04

  (EN) A derivative of 2-methylenepropane-1,3-diol of general formula (I), where O-A1 and O-A2, which can be the same or different, each represents O, O-C(O), O-C(O)NH, O-C(S)NH or O-C(O)O, R1 represents an alkyl or alkenyl group of 10 - 22 carbon atoms, n is an integer from 1 to 11, B+ represents a quaternary ammonium group, either NR4R5R6, or N(Het), where R4, R5 and R6 are similar or different alkyl groups of 1 - 4 carbon atoms, or two or all of R4, R5 and R6 may be incorporated into a cyclic or bicyclic structure, which may contain additional hetero atoms; X- means the anion of a pharmaceutically acceptable inorganic or organic acid; and R2 and R3 are the same or different, and represent hydrogen or alkyl groups of 1 - 4 carbon atoms. The present compounds have been shown to possess a PAF antagonistic effect and an inhibitory effect on the growth of tumor cells, and are thus valuable in the human and veterinary practice as platelet aggregation inhibitors, anti-thrombotic agents, anti-asthmatic agents, anti-allergic agents, anti-inflammatory agents, anti-hypotensive agents, anti-ulcer agents, anti-psoriatic agents, anti-graft rejection agents, anti-conception agents and anti-tumor agents.(FR) Dérivé de 2-méthylènepropane-1,3-diol, représenté par la formule générale (I), dans laquelle O-A1 et O-A2, qui peuvent être analogues ou différents, représentent chacun O, O-C(O), O-C(O)NH, O-C(S)NH ou O-C(O)O, R1 représente un groupe d'alkyle ou d'alkényle de 10-22 atomes de carbone, n est un nombre entier compris entre 1 et 11, B+ représente un groupe d'ammonium quaternaire, qui est soit NR4R5R6 soit N(Het), dans lequel R4, R5 et R6 sont des groupes alkyle analogues ou différents de 1-4 atomes de carbone, ou dans lequel R4, R5 et R6 peuvent tous les trois ou seulement deux d'entre eux être incorporés dans une structure cyclique ou bicyclique, laquelle peut contenir des atomes hétérogènes supplémentaires; X- représente l'anion d'un acide inorganique ou organique pharmaceutiquement acceptable; et R2 et R3 sont analogues ou différents et représentent des groupes d'hydrogène ou d'alkyle de 1-4 atomes de carbone. Lesdits composés ont révélé avoir un effet inhibiteur sur l'activité du facteur d'activation des thrombocytes (PAF) et sur la croissance des cellules tumorales. Ils peuvent par conséquent être utilisés efficacement, aussi bien en médecine humaine qu'en médecine vétérinaire, comme inhibiteurs de l'aggrégation des thrombocytes, comme agents de lutte contre la thrombose, l'asthme, les allergies, les inflammations, l'hypotension, les ulcères, le psoriasis, le rejet des greffes, les tumeurs, ainsi que comme agents contraceptifs.
• Derivatives of 2-methylenepropane-1,3-diol as new antagonists of platelet activating factor
  作者：Gunnar Grue-Soerensen、Inger Mann Nielsen、Christian Kaergaard Nielsen

  DOI：10.1021/jm00401a017

  日期：1988.6

  Two new achiral platelet activating factor (PAF) antagonists, N-[5-[[2-methylene-3- [[(octadecylamino)carbonyl]oxy]propoxy]carbonyl]pentyl]pyridinium bromide and 3-[6-[[2-methylene-3- [[(octadecylamino)carbonyl]oxy]propoxy]carbonyl]hexyl]thiazolium bromide were synthesized from 2-methylenepropane-1,3-diol. Platelet aggregation in platelet-rich plasma from rabbits, induced by racemic C16-PAF, was competitively antagonized by 9 or 10. At concentrations less than or equal to 10(-4) M, neither compound 9 nor compound 10 caused platelet aggregation, nor did they inhibit platelet aggregation induced by collagen or adenosine diphosphate. Bronchoconstriction in the guinea pig and hypotension in the rat, induced by racemic C16-PAF, were also effectively antagonized by 9 and 10. Both appear to be more potent as PAF antagonists than Takeda's CV-3988.