3-hydroxy-2-methylenepropyl N-octadecylcarbamate | 111879-26-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-hydroxy-2-methylenepropyl N-octadecylcarbamate
• 英文别名: 3-octadecylaminocarbonyloxy-2-methylenepropan-1-ol；2-(hydroxymethyl)prop-2-enyl N-octadecylcarbamate
• CAS: 111879-26-6
• 化学式: C₂₃H₄₅NO₃
• 分子量: 383.615
• InChiKey: RKGPSKQENMYEBF-UHFFFAOYSA-N

物化性质

• 熔点：
  71-73 °C(Solv: acetone (67-64-1))
• 沸点：
  512.6±43.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  27
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-methylenepropyl N-octadecylcarbamate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 2-(十八烷基氨基甲酰氧基甲基)丙-2-烯基6-吡啶-1-鎓-1-基己酸酯溴化物
  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：

  2-亚甲基-1,3-丙二醇 、 异氰酸十八酯 以 吡啶 、 水 为溶剂， 生成 3-hydroxy-2-methylenepropyl N-octadecylcarbamate
  参考文献：
  名称：

  PROPANE-1,3-DIOL DERIVATIVES, A METHOD FOR THEIR PRODUCTION AND A PHARMACEUTICAL COMPOSITION

  摘要：

  公开号：

  EP0247201B1

文献信息

• Novel propane-1,3-diol derivatives and use
  申请人：Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik

  公开号：US04945098A1

  公开（公告）日：1990-07-31

  A derivative of 2-methylenepropane-1,3-diol of the general formula I ##STR1## where O--A.sup.1 and O--A.sup.2, 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, R.sup.1 represents an alkyl or alkenyl group of 10-22 carbon atoms, n is an integer from 1 to 11, B.sup.+ represents a quaternary ammonium group, either N.sup.+ R.sup.4 R.sup.5 R.sup.6, or N.sup.+ (Het), where R.sup.4, R.sup.5 and R.sup.6 are similar or different alkyl groups of 1-4 carbon atoms, or two or all of R.sup.4, R.sup.5 and R.sup.6 may be incorporated into a cyclic or bicyclic structure, which may contain additional hetero atoms; X.sup.- means the anion of a pharmceutically acceptable inorganic or organic acid; and R.sup.2 and R.sup.3 are the same or different, and represent hydrogen or alkl 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.

  该化合物的普遍式I为：##STR1## 其中O-A.sup.1和O-A.sup.2可以相同也可以不同，每个代表O，O-C（O），O-C（O）NH，O-C（S）NH或O-C（O）O，R.sup.1代表10-22个碳原子的烷基或烯基，n为1至11的整数，B.sup.+代表季铵基，可以是N.sup.+R.sup.4R.sup.5R.sup.6或N.sup.+(Het)，其中R.sup.4，R.sup.5和R.sup.6是相似或不同的1-4个碳原子的烷基，或者其中两个或全部可以并入环状或双环结构中，其中可能含有其他杂原子；X.sup.-表示药学上可接受的无机或有机酸的阴离子；R.sup.2和R.sup.3相同或不同，代表氢或1-4个碳原子的烷基。这些化合物已被证明具有PAF拮抗作用和抑制肿瘤细胞生长的作用，在人类和兽医实践中非常有价值，可用作血小板聚集抑制剂，抗血栓剂，抗哮喘剂，抗过敏剂，抗炎剂，抗低血压剂，抗溃疡剂，抗银屑病剂，抗移植排斥剂，抗避孕剂和抗肿瘤剂。
• 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.