4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol | 161194-44-1

• 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: 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol
• 英文别名: 1-(2-chloro-ethyl)-3-[4-(4-hydroxy-butyl)-phenyl]-urea；N-(2-Chloroethyl)-N'-[4-(4-hydroxybutyl)phenyl]urea；1-(2-chloroethyl)-3-[4-(4-hydroxybutyl)phenyl]urea
• CAS: 161194-44-1
• 化学式: C₁₃H₁₉ClN₂O₂
• 分子量: 270.759
• InChiKey: WZGQIHSPCUXDHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  143-146 °C
• 沸点：
  421.3±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(4-氨基苯基)-3-丁炔-1-醇 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、262.0 kPa 条件下， 反应 20.0h， 生成 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol
  参考文献：
  名称：

  Optimized N-phenyl-N′-(2-chloroethyl)ureas as potential antineoplastic agents: Synthesis and growth inhibition activity

  摘要：

  In our ongoing research program aimed at the optimization of microtubule-self-assembly disrupting agents, we have prepared three series of phenylurea analogues (CEU), derived from N-(3-omega-hydroxyalkyl or 4-omega-hydroxyalkyl or 3-omega-hydroxyalkynyl)phenyl-N'-(2-chloroethyl)ureas. Most compounds exhibit potent growth inhibitory activity on human colon carcinoma HT-29, human skin melanoma M21, and human breast carcinoma MCF-7 tumor cell lines, with a GI(50) ranging from 250 nM to 8 mu M. Among these new molecules, three CEUs exhibit GI(50) in the nanomolar range. They are more potent by approximately an order of magnitude than previously described CEU analogues. As such, they are attractive hit compounds for the development of potent new alkylating antitubulin drugs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.048
• 作为试剂：
  描述：

  氯乙基异氰酸酯 、 4-(4-aminophenyl)butan-1-ol 在 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol 、 乙醇 、 溴化钾 作用下， 反应 3.0h， 生成 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol
  参考文献：
  名称：

  Certain carbanate anti-cancer agents

  摘要：

  本发明涉及一种新型抗癌剂，具有强效的抗肿瘤活性，且无系统毒性和致突变性。本发明的新型抗癌剂是公式I的衍生物：##STR1##其中：A为O或NH; B是苯基、茚基、芴基、吲唑基、吲哚基和吡啶基中选出的芳基基团，该芳基基团被至少一种取代基取代，所述取代基选自氢、C.sub.1-16烷基（可选地取代一个或多个OH或SH）、低烷氧基、C.sub.3-6环戊基、低烷基硫基、硝基、氰基、低烯烃、低炔烃、OH、SH、羧基低烷基、羧基低烷基酯、氨基、N-低烷基、N，N-双低烷基和卤素；或其前体药物，其中当A为NH且B为苯基时：a）B被至少一种非氢取代基取代；b）B不是：1）在4位上单取代为C.sub.1-2烷基、叔丁基或正丁基卤素、OH、羧基C.sub.0-3烷基、（CH.sub.2）.sub.3 COOCH.sub.3、氰基、乙酰基和甲硫基；2）被选自甲基卤素、硝基、甲氧基、羧基和C.sub.0-3烷基COOH的一种或两种相同的取代基取代，其余取代基为氢原子。

  公开号：

  US05750547A1

文献信息

• Certain aryl-ureido anti-cancer agents
  申请人：Universite Laval

  公开号：US05530026A1

  公开（公告）日：1996-06-25

  The present invention is concerned with novel anticancer agents having potent antineoplastic activity without systemic toxicity and mutagenicity. The novel anticancer agents of the present invention are derivatives of formula I: ##STR1## wherein: A is O or NH; and B is an aryl group selected from the group consisting of phenyl, indane, fluorene, indazole, indole, and pyridine, the aryl group being substituted with at least one substituent selected from the group consisting of hydrogen, C.sub.1-16 alkyl optionally substituted with one or more OH or SH, lower alkoxy, C.sub.3-6 cycloalkyl, lower alkylthio, nitro, cyano, lower alkene, lower alkyne, OH, SH, carboxy lower alkyl, carboxy lower alkyl esters, amino, N-lower alkyl, N,N-dilower alkyl and halogen; or a prodrug thereof, with the provisos that when A is NH and B is phenyl: a) B is substituted with at least one substituent other than hydrogen; b) B is not: 1) mono-substituted in the 4 position with C.sub.1-2 alkyl, tert-butyl or n-butyl, halogen, OH, carboxy C.sub.0-3 alkyl, (CH.sub.2).sub.3 COOCH.sub.3, cyano, acetyl and methylthio; and 2) substituted with one or two identical substituents selected from the group consisting of methyl, halogen, nitro, methoxy, carboxy and C.sub.0-3 alkyl COOH, the remaining substituents being hydrogen atoms.

  本发明涉及具有强大抗肿瘤活性而无系统毒性和诱变性的新型抗癌剂。本发明的新型抗癌剂是公式I的衍生物：其中：A为O或NH；B为从苯基、茚基、芴基、吲唑基、吲哚基和吡啶基中选择的芳基，该芳基被至少一个取代基所取代，所述取代基被选择自氢、C.sub.1-16烷基（可以选择地取代一个或多个OH或SH）、低烷氧基、C.sub.3-6环烷基、低硫基、硝基、氰基、低烯烃基、低炔烃基、OH、SH、羧基的低烷基、羧基的低烷基酯、氨基、N-低烷基、N,N-二低烷基和卤素；或其前体药物，条件是当A为NH且B为苯基时：a）B被至少一个非氢取代基取代；b）B不是：1）在4位被C.sub.1-2烷基、叔丁基或正丁基、卤素、OH、羧基的C.sub.0-3烷基、（CH.sub.2）.sub.3 COOCH.sub.3、氰基、乙酰基和甲硫基单取代；2）被选择自甲基、卤素、硝基、甲氧基、羧基和C.sub.0-3烷基COOH的一个或两个相同取代基取代，其余取代基为氢原子。
• [EN] HALOETHYL UREA COMPOUNDS AND THEIR USE TO ATTENUATE, INHIBIT OR PREVENT NON-CANCEROUS PATHOGENIC CELLULAR PROLIFERATION AND DISEASES ASSOCIATED THEREWITH<br/>[FR] COMPOSES D'UREE HALOETHYLE ET LEUR UTILISATION EN VUE D'ATTENUER, D'INHIBER OU DE PREVENIR LA PROLIFERATION CELLULAIRE PATHOGENE NON CANCEREUSE ET LES MALADIES Y ETANT ASSOCIEES
  申请人：IMOTEP INC

  公开号：WO2004106292A1

  公开（公告）日：2004-12-09

  The present invention provides haloethyl urea compounds as described in Formula (I) and their use as anti-proliferative agent in the attenuation, inhibition, or prevention of non-cancerous cellular proliferation. These compounds are also provided for use as a therapeutic agent in the treatment of a disease or disorder, wherein pathogenesis of said disease or disorder is associated with non-cancerous pathogenic cellular proliferation.

  本发明提供了如公式(I)所述的卤乙基脲化合物，以及它们作为抗增殖剂在减轻、抑制或预防非癌细胞增殖中的用途。这些化合物还可用作治疗剂，用于治疗与非癌病理性细胞增殖相关的疾病或障碍，其中该疾病或障碍的发病机制与非癌病理性细胞增殖有关。
• [EN] HALOETHYL UREA COMPOUNDS AND THE USE THEREOF TO ATTENUATE, INHIBIT OR PREVENT CANCER CELL MIGRATION<br/>[FR] COMPOSES D'UREE HALOETHYLE ET LEUR UTILISATION EN VUE D'ATTENUER, D'INHIBER OU DE PREVENIR LA MIGRATION DE CELLULES CANCEREUSES
  申请人：IMOTEP INC

  公开号：WO2004106291A1

  公开（公告）日：2004-12-09

  The present invention provides haloethyl urea compounds as described in Formula (I) and their use as therapeutic agent in the attenuation, inhibition, or prevention of cancer cell migration and cancer cell proliferation.

  本发明提供了如公式(I)所述的卤乙基脲化合物，并将其用作治疗剂，用于减轻、抑制或预防癌细胞迁移和癌细胞增殖。
• US5530026A
  申请人：——

  公开号：US5530026A

  公开（公告）日：1996-06-25
• US5750547A
  申请人：——

  公开号：US5750547A

  公开（公告）日：1998-05-12