(4S,5R)-4-methyl-5-pentadecyloxazolidin-2-one | 378755-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-4-methyl-5-pentadecyloxazolidin-2-one
• 英文别名: (4S,5R)-4-Methyl-5-(n-pentadecyl)-1,3-oxazolidinone；(4S,5R)-4-Methyl-5-(n-pentadecyl)-oxazolidinone；(4S,5R)-4-methyl-5-pentadecyl-1,3-oxazolidin-2-one
• CAS: 378755-38-5
• 化学式: C₁₉H₃₇NO₂
• 分子量: 311.508
• InChiKey: YGFQERDVWZDGKR-ZWKOTPCHSA-N

物化性质

• 沸点：
  455.2±12.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-methyl-5-pentadecyloxazolidin-2-one 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 RBM1-33
  参考文献：
  名称：

  Straightforward Access to Spisulosine and 4,5-Dehydrospisulosine Stereoisomers: Probes for Profiling Ceramide Synthase Activities in Intact Cells

  摘要：

  A stereoselective synthesis of spisulosine (ES285) and 4,5-dehydrospisulosine stereoisomers is described. Hydrozirconation of 1-pentadecyne with Schwartz reagent, followed by diastereocontrolled addition to L- or D-alaninal afforded the required 2-amino-1,3-diol framework. The resulting sphingoid bases revealed as excellent probes for the profiling of ceramide synthase activity in intact cells. Among the sphingoid bases described in this work, spisulosine (ES285), RBM1-77, and RBM1-73 were the most suitable ones because of their highest acylation rates. These molecules should prove useful to study the role of the different ceramide synthases and the resulting N-acyl (dihydro)ceramides in cell fate.

  DOI：

  10.1021/jo400440z
• 作为产物：
  描述：

  在 5wt.% Rh on activated alumina 、 氢气 、 三乙胺 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 (4S,5R)-4-methyl-5-pentadecyloxazolidin-2-one
  参考文献：
  名称：

  Straightforward Access to Spisulosine and 4,5-Dehydrospisulosine Stereoisomers: Probes for Profiling Ceramide Synthase Activities in Intact Cells

  摘要：

  A stereoselective synthesis of spisulosine (ES285) and 4,5-dehydrospisulosine stereoisomers is described. Hydrozirconation of 1-pentadecyne with Schwartz reagent, followed by diastereocontrolled addition to L- or D-alaninal afforded the required 2-amino-1,3-diol framework. The resulting sphingoid bases revealed as excellent probes for the profiling of ceramide synthase activity in intact cells. Among the sphingoid bases described in this work, spisulosine (ES285), RBM1-77, and RBM1-73 were the most suitable ones because of their highest acylation rates. These molecules should prove useful to study the role of the different ceramide synthases and the resulting N-acyl (dihydro)ceramides in cell fate.

  DOI：

  10.1021/jo400440z
• 作为试剂：
  描述：

  1-脱氧鞘氨醇(m18：0) 、 N,N'-羰基二咪唑 、 三乙胺 在 氮气 、 (4S,5R)-4-methyl-5-pentadecyloxazolidin-2-one 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (4S,5R)-4-methyl-5-pentadecyloxazolidin-2-one
  参考文献：
  名称：

  Spisulosine compounds

  摘要：

  对蛤蜊Spisula polynyma提取物活性的研究发现，存在具有2-氨基和3-羟基的长链、直链烷烃或烯烃抗肿瘤化合物。

  公开号：

  US20040147615A1

文献信息

• Antitumoral compounds
  申请人：——

  公开号：US20040048834A1

  公开（公告）日：2004-03-11

  New spisulosine derivatives of use in treating tumors are of the formula (I) wherein: each X is the same or different, and represents H, OH, OR′, SH, SR′, SOR′, SO 2 R′, NO 2 , NH 2 , NHR′, N(R′) 2 , CN, halogen, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups X may together form ═O; Y is NR 1 , OR 1 , PR 1 , SR 1 , or halogen, wherein the number of substituents R 1 is selected to suit the valency and each R 1 is independently selected of H, OH, C(═O)R′, P(═O)R′R″, substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, and wherein the dotted line indicates an optional double bond; each Z is the same different, and represents H, OH, OR′, SH, SR′, SOR′, SO 2 R′, NO 2 , NH 2 , NHR′, N(R′) 2 , NHC(O)R′, CN, halogen, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups Z may together form ═O; z is 0 to 25; y is to 0 to 20; R 2 is H, C(═O)R′, P(═O)R′R″, S(═O)R′R″, S(═O) 2 R′, substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 Alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl; R 3 is H, C(═O)R′, P(═O)R′R″, S(═O)R′R″, S(═O) 2 R′, substituted or unsubstituted C 1 -C 18 alklyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl; each of the R′, R″ groups is independently selected from the group consisting of H, OH, NO 2 , NH 2 , SH, CN, halogen, ═O, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 1 -C 18 alkoxy, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynl, substituted or unsubstituted aryl; there may be one or more unsaturations in the hydrocarbon backbone defined by the chain (II) and salts thereof; with the exception of a C 16 -C 24 2-amino-3-hydroxyalkane or a C 16 -C 24 2-amino-3-hydroxyalkene.

  新的用于治疗肿瘤的斯皮苏林衍生物的化学式为（I），其中：每个X相同或不同，表示H、OH、OR′、SH、SR′、SOR′、SO2R′、NO2、NH2、NHR′、N(R′)2、CN、卤素、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基、取代或未取代的杂芳基，或两个X基团可能共同形成═O；Y为NR1、OR1、PR1、SR1或卤素，其中取代基R1的数量选择以适应化合价，每个R1独立选择自H、OH、C(═O)R′、P(═O)R′R″、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基，虚线表示可选的双键；每个Z相同或不同，表示H、OH、OR′、SH、SR′、SOR′、SO2R′、NO2、NH2、NHR′、N(R′)2、NHC(O)R′、CN、卤素、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基、取代或未取代的杂芳基，或两个Z基团可能共同形成═O；z为0至25；y为0至20；R2为H、C(═O)R′、P(═O)R′R″、S(═O)R′R″、S(═O)2R′、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；R3为H、C(═O)R′、P(═O)R′R″、S(═O)R′R″、S(═O)2R′、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；每个R′、R″基团独立选择自H、OH、NO2、NH2、SH、CN、卤素、═O、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C1-C18烷氧基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；碳链（II）中的碳氢骨架中可能存在一个或多个不饱和度，及其盐；除了C16-C242-氨基-3-羟基烷或C16-C242-氨基-3-羟基烯。
• COMPOSITIONS AND METHODS COMPRISING LONG-CHAIN, STRAIGHT-CHAIN 2-AMINO-3- HYDROXYALKANES
  申请人：Rinehart L. Kenneth

  公开号：US20060183806A9

  公开（公告）日：2006-08-17

  Investigation of the activity of extracts of the clam Spisula polynyma has led to antitumour long-chain, straight-chain alkane or alkene compounds which have a 2-amino group and a 3-hydroxy group.

  对蛤蜊Spisula polynyma提取物活性的研究表明，含有2-氨基和3-羟基的长链、直链烷或烯化合物具有抗肿瘤活性。
• Long-chain, straight-chain 2-amino-3-hydroxyalkanes
  申请人：Rinehart L. Kenneth

  公开号：US20060235082A1

  公开（公告）日：2006-10-19

  Investigation of the activity of extracts of the clam Spisula polynyma has led to antitumor long-chain, straight-chain alkane compounds which have a 2-amino group and a 3-hydroxy group. Compositions and methods comprising an isolated and purified long-chain, straight-chain 2-amino-3-hydroxyalkane, or prodrug thereof, and a pharmaceutically acceptable carrier are also described, wherein the carbon chain in the long-chain, straight-chain 2-amino-3-hydroxyalkane is C 16 -C 24 .

  对Spisula polynyma蛤的提取物活性的研究已经发现了具有2-氨基和3-羟基的抗肿瘤长链直链烷化合物。还描述了包含分离和纯化的长链直链2-氨基-3-羟基烷或其前药及药学可接受载体的组合物和方法，其中长链直链2-氨基-3-羟基烷中的碳链为C16-C24。
• ANTITUMORAL COMPOUNDS
  申请人：PHARMA MAR, S.A.

  公开号：EP1287006B1

  公开（公告）日：2007-10-24
• US7109244B2
  申请人：——

  公开号：US7109244B2

  公开（公告）日：2006-09-19