(N,N-bis-2-chloroethylaminophenyl)propylamine | 129787-13-9

• 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-bis-2-chloroethylaminophenyl)propylamine
• 英文别名: 4-(N,N-bis(2-chloroethyl)-amino)phenyl-propylamine；4-(3-aminopropyl)-N,N-bis(2-chloroethyl)aniline；3-[4-[N,N-bis(2-chloroethyl)amino]-phenyl]-propylamine；3-[4-[N,N-Bis(2-chloroethyl)amino]phenyl]propylamine
• CAS: 129787-13-9
• 化学式: C₁₃H₂₀Cl₂N₂
• 分子量: 275.221
• InChiKey: BJDIQIYTNNHVRY-UHFFFAOYSA-N

物化性质

• 沸点：
  403.3±45.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (N,N-bis-2-chloroethylaminophenyl)propylamine 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 3-{p-[bis(2-chloroethyl)amino]phenyl}propylamine hydrochloride
  参考文献：
  名称：

  Methods and compositions for treating cancer

  摘要：

  这项发明提供了用于治疗癌症的化合物和方法。示例化合物是具有两种不同基团通过连接剂连接的多功能化合物。该发明的化合物可以激活导致细胞生长抑制的一个或多个途径。该发明包括细胞静止和细胞毒性化合物。该发明的方法和组合物特别适用于治疗对其他化疗药物具有抗药性的癌细胞。

  公开号：

  US20060019936A1
• 作为产物：
  描述：

  苯丁酸氮芥 在 盐酸 、 sodium azide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 丙酮 、 苯 为溶剂， 反应 1.92h， 生成 (N,N-bis-2-chloroethylaminophenyl)propylamine
  参考文献：
  名称：

  DNA-directed alkylating agents. 3. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the length of the linker chain

  摘要：

  Four series of acridine-linked aniline mustards have been prepared and evaluated for in vitro cytotoxicity, in vivo antitumor activity, and DNA cross-linking ability. The anilines were attached to the DNA-intercalating acridine chromophores by link groups (-O-, -CH2-, -S-, and -SO2-) of widely varying electronic properties, providing four series of widely differing mustard reactivity where the alkyl chain linking the acridine and mustard moieties was varied from two to five carbons. Relationships were sought between chain length and biological properties. Within each series, increasing the chain length did not alter the reactivity of the alkylating moiety but did appear to position it differently on the DNA, since cross-linking ability (measured by agarose gel assay) altered with chain length, being maximal with the C4 analogue. The in vivo antitumor activities of the compounds depended to some extent on the reactivity of the mustard, with the least reactive SO2 compounds being inactive. However, DNA-targeting did appear to allow the use of less reactive mustards, since the S-linked acridine mustards showed significant activity whereas the parent S-mustard did not. Within each active series, the most active compound was the C4 homologue, suggesting some relationship between activity and extent of DNA alkylation.

  DOI：

  10.1021/jm00173a016

文献信息

• Synthesis and Cytotoxic Activity of Novel Amidine Analogues of Bis(2-chloroethyl)amine
  作者：Krzysztof Bielawski、Anna Bielawska、Bozena Poplawska

  DOI：10.1002/ardp.200800231

  日期：2009.8

  in‐vitro cytotoxic activity against MDA‐MB‐231 and MCF‐7 human breast cancer cells. Evaluation of the cytotoxicity of 7–12 employing a MTT assay and inhibition of [3H]thymidine incorporation into DNA demonstrated that these compounds exhibit remarkable cytotoxic effects in comparison with 4‐[bis(2‐chloroethyl)amino]benzenebutanoic acid. Compounds 7 and 9, which possess a cationic amidine and 4,5‐dihydro‐1H‐imidazol

  新型氮芥剂 7-12 涉及 4-(N,N-双(2-氯乙基)氨基苯基)丙胺通过形成酰胺键连接到 5-(4-N-烷基脒基苯基)-2-呋喃甲酸部分具有合成、表征并评估了它们对 MDA-MB-231 和 MCF-7 人乳腺癌细胞的体外细胞毒活性。使用 MTT 测定和抑制 [3H] 胸苷掺入 DNA 评估 7-12 的细胞毒性表明，与 4-[双（2-氯乙基）氨基]苯丁酸相比，这些化合物表现出显着的细胞毒性作用。化合物 7 和 9 具有阳离子脒和 4,5-二氢-1H-咪唑官能团，其效力大约是 4-[双（2-氯乙基）氨基]苯丁酸的 10 倍。新化合物被评估为 DNA 拓扑异构酶 II 抑制剂。
• Linker structure-activity relationships in fluorodeoxyglucose chlorambucil conjugates for tumor-targeted chemotherapy
  作者：Mostafa El Hilali、Bastien Reux、Eric Debiton、Fernand Leal、Marie-Josephe Galmier、Magali Vivier、Jean-Michel Chezal、Elisabeth Miot-Noirault、Pascal Coudert、Valérie Weber

  DOI：10.1016/j.bmc.2017.08.043

  日期：2017.10

  glucoconjugates 2 and 3 with promising antitumor activities in vivo. These results prompted us to investigate the importance of the spacer in this tumor-targeting glucose-based conjugates. Here we report the chemical synthesis and an in vitro cytotoxicity evaluation, using a 5-member panel of human tumor cell lines and human fibroblasts, of 16 new CLB glucoconjugates in which the alkylating drug is attached to

  氮芥，例如苯丁酸氮芥（CLB），由于在非目标器官中普遍分布而可能引起不利的副作用。为了最小化这种毒性，已经开发了靶向肿瘤的药物递送策略，其中细胞毒性弹头与肿瘤细胞特异性小配体相连。恶性细胞通过有氧糖酵解表现出明显的葡萄糖亲和力和加速的代谢，这被称为Warburg效应，被认为是癌症的标志。先前已经报道了一种通过将CLB与2-氟-2-脱氧葡萄糖（FDG）结合来利用Warburg效应的靶向方法，并确定了两种在体内具有有希望的抗肿瘤活性的过乙酰化葡萄糖结合物2和3 。。这些结果促使我们研究间隔子在这种靶向肿瘤的基于葡萄糖的结合物中的重要性。在这里，我们报告了16种新的CLB葡萄糖缀合物的化学合成和体外细胞毒性评估，该评估是使用人类肿瘤细胞系和人类成纤维细胞的5人小组进行的，其中烷基化药物通过不同的方式连接到FDG的C-1位置联系。我们研究了接头中的结构-活性关系，并证明了芳香族接头对体外细胞毒性的
• Programmable genotoxic agents and uses therefor
  申请人：——

  公开号：US20030220311A1

  公开（公告）日：2003-11-27

  The compositions and methods disclosed herein provide heterobifunctional programmable genotoxic compounds that can be designed to kill selected cells present in a heterogenous cell population. The present compounds comprise a first agent that inflicts damage on cellular DNA, and a second agent that attracts a macromolecular cell component such as a protein, which in turn shields genomic lesions from repair. Unrepaired lesions therefore persist in the cellular genome and contribute to the death of selected cells. In contrast, lesions formed in nonselected cells, which lack the cell component, are unshielded and thus are repaired. As a result, compounds described herein are less toxic to nonselected cells. Compounds of this invention can be designed to cause the selective killing of transformed cells, viral-infected cells and the like.

  本文所披露的组合物和方法提供了异双功能可编程基因毒性化合物，可以设计用于杀死杂种细胞群落中的选择性细胞。目前的化合物包括第一种对细胞DNA造成损伤的药剂和第二种吸引大分子细胞组分（例如蛋白质）的药剂，该组分反过来又保护基因组损伤不受修复。因此，未修复的损伤会在细胞基因组中持续存在，并有助于选择性细胞的死亡。相比之下，形成在缺乏细胞组分的非选择性细胞中的损伤是未被保护的，因此会得到修复。因此，本文所述的化合物对非选择性细胞的毒性较小。本发明的化合物可以被设计用于选择性杀死转化细胞、病毒感染细胞等。
• Benzimidazole derivatives
  申请人：Mitsui Chemicals, Inc.

  公开号：US05852011A1

  公开（公告）日：1998-12-22

  Disclosed are compounds represented by the following chemical formula (I) and pharmacologically acceptable salts thereof which are novel compounds useful as anticancer agents, antiviral agents or antimicrobial agents. ##STR1##

  本发明涉及以下化学式（I）所表示的化合物及其药理学上可接受的盐，这些新型化合物可用作抗癌剂、抗病毒剂或抗微生物剂。 ##STR1##
• BENZIMIDAZOLE DERIVATIVE
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0711768A1

  公开（公告）日：1996-05-15

  Disclosed are compounds represented by the following chemical formula (I) and pharmacologically acceptable salts thereof which are novel compounds useful as anticancer agents, antiviral agents or antimicrobial agents.

  所公开的是由以下化学式（I）代表的化合物及其药理学上可接受的盐类，它们是可用作抗癌剂、抗病毒剂或抗菌剂的新型化合物。