N-(3-morpholin-4-yl-propyl)-benzene-1,2-diamine | 62553-49-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-morpholin-4-yl-propyl)-benzene-1,2-diamine
• 英文别名: N-(3-Morpholinopropyl)-1,2-benzenediamine；2-(3-morpholinopropylamino)-aniline；N-(3-morpholino-propyl)-o-phenylenediamine；N-(3-Morpholino-propyl)-o-phenylendiamin；N-[3-(N-morpholino)propyl]-o-phenylenediamine；n1-(3-Morpholinopropyl)benzene-1,2-diamine；2-N-(3-morpholin-4-ylpropyl)benzene-1,2-diamine
• CAS: 62553-49-5
• 化学式: C₁₃H₂₁N₃O
• mdl: MFCD10699321
• 分子量: 235.329
• InChiKey: IIISXLQLWIFUIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  50.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻氯苯氧乙酸 、 N-(3-morpholin-4-yl-propyl)-benzene-1,2-diamine 在 N,N'-羰基二咪唑 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 2-(2-chloro-phenoxymethyl)-1-(3-morpholin-4-yl-propyl)-1H-benzimidazole
  参考文献：
  名称：

  Parallel synthesis of a series of potentially brain penetrant aminoalkyl benzoimidazoles

  摘要：

  Alpha7 agonists were identified via GOLD (CCDC) docking in the putative agonist binding site of an alpha7 homology model and a series of aminoalkyl benzoimidazoles was synthesised to obtain potentially brain penetrant drugs. The array was prepared starting from the reaction of ortho-fluoronitrobenzenes with a selection of diamines, followed by reduction of the nitro group to obtain a series of monoalkylated phenylene diamines. N,N'-Carbonyidiimidazole (CDI) mediated acylation, followed by a parallel automated work-up procedure, afforded the monoacylated phenylenediamines which were cyclised under acidic conditions. Parallel work-up and purification afforded the array products in good yields and purities with a robust parallel methodology which will be useful for other libraries. Screening for alpha7 activity revealed compounds with agonist activity for the receptor. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.068
• 作为产物：
  描述：

  (3-morpholin-4-yl-propyl)-(2-nitro-phenyl)-amine 在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-(3-morpholin-4-yl-propyl)-benzene-1,2-diamine
  参考文献：
  名称：

  苯并咪唑衍生物作为新型寨卡病毒抑制剂。

  摘要：

  我们在温和的氧化条件下，通过廉价的无毒无机盐偏亚硫酸氢钠在一锅缩合反应中合成了50种苯并咪唑（BMZ）衍生物与1,2-苯二胺和芳族醛，并筛选了它们干扰寨卡病毒（ZIKV）的能力利用基于细胞的表型分析进行感染。七个BMZ抑制非洲ZIKV菌株的选择性指数（SI = CC 50 / EC 50）的9–37。结构活性关系分析表明，在BMZ环的C-2，N-1和C-5位置进行取代对于抗ZIKV活性很重要。BMZ和萘环的杂化结构是导致高抗ZIKV活性的结构特征。重要的是，BMZ抑制了人类神经干细胞中的ZIKV，这是一种生理相关系统，考虑到ZIKV感染引起的严重先天性异常，如小头畸形。在Huh-7（SI> 37）和神经干细胞（SI = 12）中，化合物39对非洲ZIKV株显示出最高的抗病毒效力。化合物35在Vero细胞中具有最高的活性（SI = 115）。总之，我们的数据表明在开发ZIKV治疗干预措施时必须考虑BMZs衍生物。

  DOI：

  10.1002/cmdc.202000124

文献信息

• Benzimidazole derivative, hair growth promoter and external composition for skin using the same
  申请人：Shiseido Co., Ltd.

  公开号：US06204264B1

  公开（公告）日：2001-03-20

  A benzimidazole derivative or a salt thereof expressed by the following Formula (I): wherein one of A and B is a hydrocarbon group of C10-30 expressed by R1 and the other is —(CH2)n—NR2R3; R2 and R3 individually represent H, lower alkyl, phenyl or benzyl, or —NR2R3 may be a heterocycle having 3-7 members, or —CONR5—(CH2)n—NR2R3 may be the following Group (W): wherein R2 is H, lower alkyl, phenyl or benzyl and ring E is a heterocycle of 6 or 7 members; R4 is selected from the group consisting of H, halogen, cyano, trifluoromethyl, lower alkyl and etc.; R5 is H, lower alkyl, lower acyl or lower alkylcarbamoyl; m is 0 or 1; and n is an integer of 0-5. The benzimidazole derivative or the salt thereof has excellent hair growth and regrowth promoting effects, which are useful for care, improvement or prevention of hair loss in mammals and, in particular, in human.

  一种苯并咪唑衍生物或其盐，由以下式（I）表示：其中A和B中的一个是由R1表示的C10-30的烃基，另一个是—（CH2）n—NR2R3；R2和R3分别代表H、较低的烷基、苯基或苄基，或者—NR2R3可以是具有3-7个成员的杂环，或者—CONR5—（CH2）n—NR2R3可以是以下的基团（W）：其中R2为H、较低的烷基、苯基或苄基，环E为6或7个成员的杂环；R4选自H、卤素、氰基、三氟甲基、较低的烷基等组成的群；R5为H、较低的烷基、较低的酰基或较低的烷基甲酰基；m为0或1；n为0-5的整数。该苯并咪唑衍生物或其盐具有出色的促进头发生长和再生的效果，可用于哺乳动物的护理、改善或预防脱发，特别是人类。
• Design, synthesis and biological evaluation of novel 7-alkylamino substituted benzo[a]phenazin derivatives as dual topoisomerase I/II inhibitors
  作者：Bing-Lei Yao、Yan-Wen Mai、Shuo-Bin Chen、Hua-Ting Xie、Pei-Fen Yao、Tian-Miao Ou、Jia-Heng Tan、Hong-Gen Wang、Ding Li、Shi-Liang Huang、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2015.01.024

  日期：2015.3

  A novel series of benzo[a]phenazin derivatives bearing alkylamino side chains were designed, synthesized and evaluated for their topoisomerases inhibitory activity as well as cytotoxicity against four human cancer cell lines (HL-60, K-562, HeLa, and A549). These compounds were found to be dual inhibitors of topoisomerase (Topo) I and Topo II, and exhibited excellent antiproliferative activity, in particular against HL-60 cells with submicromolar IC50 values. Further mechanistic studies showed that this class of compounds acted as Topo I poisons by stabilizing the Topo I-DNA cleavage complexes and Topo II catalytic inhibitors by inhibiting the ATPase activity of hTopo II. Molecular docking studies revealed the binding modes of these compounds for Topo I and Topo II. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Heterocyclic Basic Compounds. VII. Basically-substituted Isoalloxazine Derivatives¹
  作者：Robert R. Adams、Charles A. Weisel、Harry S. Mosher

  DOI：10.1021/ja01209a055

  日期：1946.5
• Rufer,C. et al., Chimica Therapeutica, 1971, vol. 6, p. 286 - 291
  作者：Rufer,C. et al.

  DOI：——

  日期：——
• US4002623A
  申请人：——

  公开号：US4002623A

  公开（公告）日：1977-01-11