(+/-)-N,N-dibenzyl-2-aminopentan-1-ol | 750592-65-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-N,N-dibenzyl-2-aminopentan-1-ol
• 英文别名: 2-(dibenzylamino)pentan-1-ol
• CAS: 750592-65-5
• 化学式: C₁₉H₂₅NO
• 分子量: 283.414
• InChiKey: UUOVWTITZBZUOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-N,N-dibenzyl-2-aminopentan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (+/-)-N,N-dibenzyl-3-aminohexan-2-ol
  参考文献：
  名称：

  4,5-Dialkylsubstituted 2-imino-1,3-thiazolidine derivatives as potent inducible nitric oxide synthase inhibitors

  摘要：

  In the course of our search for selective iNOS inhibitors, we have previously reported that 2-imino-1,3-oxazolidine derivatives (1) and 2-aminothiazole derivatives (2) are selective iNOS inhibitors. In order to find more potent iNOS inhibitors, we focused our efforts on the synthesis and evaluation of the inhibitory activity against iNOS and selectivity for iNOS both in vitro and in vivo of a series of 2-imino-1,3-thiazolidine derivatives (3), which are analogues of I and 2. Our results show that among the compounds synthesized (4R,5R)-5-ethyl-2-imino-4-methyl-1,3-thiazolidine [(4R,5R)-14a: ES-1537] exhibited potent inhibitory activity and selectivity for iNOS. In addition, ES-1537 had good pharmacokinetic profile in rats with BA value of 80%. It is therefore expected that ES-1537 may be therapeutically useful for the treatment of diseases related to excess production of NO. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.031
• 作为产物：
  描述：

  DL-2-氨基-1-戊醇 、 溴甲苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以69.4%的产率得到(+/-)-N,N-dibenzyl-2-aminopentan-1-ol
  参考文献：
  名称：

  氮丙啶鎓离子的立体选择性和区域选择性分子内傅克反应合成 4-取代四氢异喹啉

  摘要：

  通过氮丙啶鎓离子的分子内弗里德尔-克来福特 (FC) 反应以高度区域和立体选择性方式合成了光学活性 4-取代四氢异喹啉。对照实验表明氮丙啶鎓离子的形成和开环是路易斯酸催化 FC 反应中的关键中间体。

  DOI：

  10.1021/ol4013537

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。
• ANTITUMORAL COMPOUNDS
  申请人：PHARMA MAR, S.A.

  公开号：EP1287006B1

  公开（公告）日：2007-10-24
• US7138547B2
  申请人：——

  公开号：US7138547B2

  公开（公告）日：2006-11-21
• Stereoselective and Regioselective Intramolecular Friedel–Crafts Reaction of Aziridinium Ions for Synthesis of 4-Substituted Tetrahydroisoquinolines
  作者：Hyun-Soon Chong、Yunwei Chen

  DOI：10.1021/ol4013537

  日期：2013.12.6

  Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel–Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziridinium ions as the key intermediates in the Lewis acid catalyzed FC reactions.

  通过氮丙啶鎓离子的分子内弗里德尔-克来福特 (FC) 反应以高度区域和立体选择性方式合成了光学活性 4-取代四氢异喹啉。对照实验表明氮丙啶鎓离子的形成和开环是路易斯酸催化 FC 反应中的关键中间体。
• 4,5-Dialkylsubstituted 2-imino-1,3-thiazolidine derivatives as potent inducible nitric oxide synthase inhibitors
  作者：Shigeo Ueda、Hideo Terauchi、Akihiro Yano、Masashi Matsumoto、Taeko Kubo、Yoko Kyoya、Kenji Suzuki、Motoharu Ido、Motoji Kawasaki

  DOI：10.1016/j.bmc.2004.05.031

  日期：2004.8.1

  In the course of our search for selective iNOS inhibitors, we have previously reported that 2-imino-1,3-oxazolidine derivatives (1) and 2-aminothiazole derivatives (2) are selective iNOS inhibitors. In order to find more potent iNOS inhibitors, we focused our efforts on the synthesis and evaluation of the inhibitory activity against iNOS and selectivity for iNOS both in vitro and in vivo of a series of 2-imino-1,3-thiazolidine derivatives (3), which are analogues of I and 2. Our results show that among the compounds synthesized (4R,5R)-5-ethyl-2-imino-4-methyl-1,3-thiazolidine [(4R,5R)-14a: ES-1537] exhibited potent inhibitory activity and selectivity for iNOS. In addition, ES-1537 had good pharmacokinetic profile in rats with BA value of 80%. It is therefore expected that ES-1537 may be therapeutically useful for the treatment of diseases related to excess production of NO. (C) 2004 Elsevier Ltd. All rights reserved.