N,N-双(2-氯乙基)-p-硝基-苄胺盐酸盐 | 40136-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-双(2-氯乙基)-p-硝基-苄胺盐酸盐
• 英文名称: bis(2-chloroethyl)-(4-nitrobenzyl)amine hydrochloride
• 英文别名: Bis-(2-chlor-aethyl)-(4-nitro-benzyl)-amin; Hydrochlorid；N,N-bis(2-Chloroethyl)-p-nitro-benzylamine hydrochloride；2-chloro-N-(2-chloroethyl)-N-[(4-nitrophenyl)methyl]ethanamine;hydrochloride
• CAS: 40136-95-6
• 化学式: C₁₁H₁₄Cl₂N₂O₂*ClH
• 分子量: 313.611
• InChiKey: JDIDLDRXEFSBCW-UHFFFAOYSA-N

物化性质

• 熔点：
  138-148 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.54
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  50.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  N,N-双(2-氯乙基)-p-硝基-苄胺盐酸盐 在 盐酸 、 tin(ll) chloride 作用下， 反应 0.5h， 生成 p-Amino-N,N-bis-(2-chlorethyl)-benzylamin
  参考文献：
  名称：

  Potent antitumor 9-anilinoacridines bearing an alkylating N-mustard residue on the anilino ring: synthesis and biological activity

  摘要：

  A series of N-mustard derivatives of 9-anilinoacridine was synthesized for antitumor and structure-activity relationship studies. The alkylating N-mustard residue was linked to the C-3' or C-4' position of the anilino ring with an O-ethylene (O-C-2) O-butylene (O-C-4), and methylene (C-1) spacer. All of the new N-mustard derivatives exhibited significant cytotoxicity in inhibiting human lymphoblastic leukemic cells (CCRF-CEM) in culture. Of these agents, (3-(acridin-9-ylamino)-5-{2-[bis(2-chloroethyl)amino]ethoxy}phenyl)methanol (10) was subjected to antitumor studies, resulting in an approximately 100-fold more potent effect than its parent analogue 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA) in inhibiting the growth of human lymphoblastic leukemic cells (CCRF-CEM) in vitro. This agent did not exhibit cross-resistance against vinblastine-resistant (CCRF-CEM/VBL) or Taxol-resistant (CCRF-CEM/Taxol) cells. Remarkably, the therapeutic effect of 10 at a dose as low as one tenth of the Taxol therapeutic dose [i.e., 1-2 mg/kg (Q3D x 7) or 3 mg/kg (Q4D x 5); intravenous injection] on nude mice bearing human breast carcinoma MX-1 xenografts resulted in complete tumor remission in two out of three mice. Furthermore, 10 yielded xenograft tumor suppression of 81-96% using human T-cell acute lymphoblastic leukemia CCRF-CEM, colon carcinoma HCT-116, and ovarian adenocarcinoma SK-OV-3 tumor models. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.057
• 作为产物：
  描述：

  2-[(2-hydroxyethyl)-(4-nitrobenzyl)amino]ethanol 在 氯化亚砜 、 氯仿 作用下， 生成 N,N-双(2-氯乙基)-p-硝基-苄胺盐酸盐
  参考文献：
  名称：

  Ishidate et al., Pharmaceutical Bulletin, 1957, vol. 5, p. 203

  摘要：

  DOI：

文献信息

• Nitrogen Mustards
  作者：Evelyn Wilson、Max Tishler

  DOI：10.1021/ja01152a023

  日期：1951.8
• Potent antitumor 9-anilinoacridines bearing an alkylating N-mustard residue on the anilino ring: synthesis and biological activity
  作者：Valeriy A. Bacherikov、Ting-Chao Chou、Hua-Jin Dong、Xiuguo Zhang、Ching-Huang Chen、Yi-Wen Lin、Tsong-Jen Tsai、Rong-Zau Lee、Leroy F. Liu、Tsann-Long Su

  DOI：10.1016/j.bmc.2005.03.057

  日期：2005.6

  A series of N-mustard derivatives of 9-anilinoacridine was synthesized for antitumor and structure-activity relationship studies. The alkylating N-mustard residue was linked to the C-3' or C-4' position of the anilino ring with an O-ethylene (O-C-2) O-butylene (O-C-4), and methylene (C-1) spacer. All of the new N-mustard derivatives exhibited significant cytotoxicity in inhibiting human lymphoblastic leukemic cells (CCRF-CEM) in culture. Of these agents, (3-(acridin-9-ylamino)-5-2-[bis(2-chloroethyl)amino]ethoxy}phenyl)methanol (10) was subjected to antitumor studies, resulting in an approximately 100-fold more potent effect than its parent analogue 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA) in inhibiting the growth of human lymphoblastic leukemic cells (CCRF-CEM) in vitro. This agent did not exhibit cross-resistance against vinblastine-resistant (CCRF-CEM/VBL) or Taxol-resistant (CCRF-CEM/Taxol) cells. Remarkably, the therapeutic effect of 10 at a dose as low as one tenth of the Taxol therapeutic dose [i.e., 1-2 mg/kg (Q3D x 7) or 3 mg/kg (Q4D x 5); intravenous injection] on nude mice bearing human breast carcinoma MX-1 xenografts resulted in complete tumor remission in two out of three mice. Furthermore, 10 yielded xenograft tumor suppression of 81-96% using human T-cell acute lymphoblastic leukemia CCRF-CEM, colon carcinoma HCT-116, and ovarian adenocarcinoma SK-OV-3 tumor models. (c) 2005 Elsevier Ltd. All rights reserved.
• Ishidate et al., Pharmaceutical Bulletin, 1957, vol. 5, p. 203
  作者：Ishidate et al.

  DOI：——

  日期：——