N¹,N¹-bis(2-chloroethyl)benzene-1,3-diamine | 13686-19-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N¹,N¹-bis(2-chloroethyl)benzene-1,3-diamine
• 英文别名: 3-N,3-N-bis(2-chloroethyl)benzene-1,3-diamine
• CAS: 13686-19-6
• 化学式: C₁₀H₁₄Cl₂N₂
• 分子量: 233.141
• InChiKey: HEOXTQZNZQKYIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  N¹,N¹-bis(2-chloroethyl)benzene-1,3-diamine 在 sodium hydroxide 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 3.0h， 生成 4-(3-(bis(2-chloroethyl)amino)phenylamino)-7-methoxyquinazolin-6-ol
  参考文献：
  名称：

  新型喹唑啉氮芥菜衍生物的设计和合成作为潜在的癌症治疗剂

  摘要：

  设计，合成和评估了十三种新颖的喹唑啉氮芥子气衍生物在体外和体内的抗癌活性。在五种癌细胞系（HepG2，SH-SY5Y，DU145，MCF-7和A549）和一种正常人细胞系（GES-1）中进行了细胞毒性测定，其中化合物22b对HepG2的IC 50非常低（ IC 50值为3.06μM），低于索拉非尼。化合物22b可以抑制S和G 2 / M期的细胞周期并诱导细胞凋亡。在HepG2异种移植模型中，22b在体内具有显着的癌生长抑制作用，且宿主毒性低。

  DOI：

  10.1016/j.ejmech.2013.06.055
• 作为产物：
  描述：

  N,N-bis(2-(methylsulfonyloxy)ethyl)-3-nitroaniline 在 palladium 10% on activated carbon 、 氢气 、 lithium chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N¹,N¹-bis(2-chloroethyl)benzene-1,3-diamine
  参考文献：
  名称：

  吡唑并[1,5-a]嘧啶氮芥衍生物及其制备方法 和肿瘤治疗应用

  摘要：

  本发明涉及具有式I结构的吡唑并[1，5‑a]嘧啶氮芥衍生物或其可药用盐，以及其用途。药理实验表明，该类化合物或其可药用盐对多种肿瘤细胞的增殖具有抑制作用。不仅如此，该类化合物还具有毒性较小，对肿瘤细胞具有选择性的优势，是一种具有双功能的抗肿瘤药物。同时，该类化合物易于合成，总产率较高。种种优势，显示此类化合物具有成为肿瘤治疗药物的巨大潜力。

  公开号：

  CN103626776B

文献信息

• 新型喹唑啉氮芥类化合物及其制备方法和肿瘤 治疗应用
  申请人：北京师范大学

  公开号：CN103193722B

  公开（公告）日：2016-02-24

  一种新型喹唑啉氮芥类化合物，其特征在于：一端具有氮芥烷化基团；另一端具有6，7-取代的喹唑啉结构，取代基R1位于喹唑啉母体4位上，为2-、3-、4-的氮芥基团；取代基R2、R3分别位于喹唑啉母体的6，7位上，为甲氧乙氧基、甲氧基、吗啡啉丙氧基、3-四氢呋喃氧基及羟基。结构如式A。实验表明，该类化合物能造成DNA的交联，是一种双功能烷化剂。体内抗肿瘤活性实验表明，该类化合物具有较好的活性。不仅如此，该类化合物还具有氮芥类药物所没有的优势，即毒性较小。同时，该类化合物易于合成，总产率较高。种种优势，显示此类化合物具有成为肿瘤治疗药物的巨大潜力。
• Cytotoxic compounds. Part X. Carbamates derived from NN-bis-(2-chloroethyl)-m- and NN-bis-(2-chloroethyl)-p-phenylenediamine
  作者：L. N. Owen、R. Sridhar

  DOI：10.1039/j39700000472

  日期：——

  Urethanes have been prepared by reaction of the amines m-RNH2 or p-RNH2[R = C6H4·N(CH2·CH2Cl)2] with chloroformates. The products, after removal of protecting groups, include p-RNH·CO·O·C6H4·CO2H (o-, m-, and p-), m-RNH·CO·O·C6H4·CO2H(m-), O-(p-RNH·CO)-serine, and O-(p-RNH·CO)-threonine. Terephthalic amides, (p-RNH·CO)2C6H4 and (p-RNH·CO)C6H4·CO2Me, and phthalimides, C6H4(CO)2NR (m- and p-), are also

  通过使胺m -RNH 2或对-RNH 2 [R = C 6 H 4 ·N（CH 2 ·CH 2 Cl）2 ]与氯甲酸酯反应制备氨基甲酸酯。该产品，除去保护基团后，包括p -RNH·CO·O·C ^ 6 ħ 4 ·CO 2 H（ø - ，米- ，和p - ），米-RNH·CO·O·C ^ 6 ħ 4 ·CO 2 H（m -），O-（p-RNH·CO）-丝氨酸和O-（p -RNH·CO）-苏氨酸。对苯二甲酸酰胺，（p -RNH·CO）2 C ^ 6 ħ 4和（p -RNH·CO）C 6 H ^ 4 ·CO 2 Me和邻苯二甲酰亚胺，C 6 H ^ 4（CO）2 NR（米-和p - ），也有介绍。
• 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。
• Enhanced oral and transcompartmental delivery of therapeutic or diagnostic agents
  申请人：——

  公开号：US20030091640A1

  公开（公告）日：2003-05-15

  The invention is directed to pharmaceutical compositions and methods for delivery of a therapeutic or diagnostic agent from one bodily compartment to one or more other bodily compartment by administering one of the following conjugates: a polymer having multiple functional groups at least one of which is covalently bound to a therapeutic or diagnostic agent, and at least one cell uptake promoter covalently bound to the therapeutic or diagnostic agent; or a polymer and at least one cell uptake promoter bound thereto; the polymer further comprising multiple functional groups at least one of which is covalently bound a therapeutic or diagnostic agent.

  本发明涉及通过施用下列共轭物之一将治疗剂或诊断剂从一个体腔输送到一个或多个其他体腔的药物组合物和方法：具有多个官能团（其中至少有一个官能团与治疗剂或诊断剂共价结合）的聚合物，以及至少一个与治疗剂或诊断剂共价结合的细胞摄取促进剂；或聚合物和至少一个与之结合的细胞摄取促进剂；聚合物进一步包含多个官能团（其中至少有一个官能团与治疗剂或诊断剂共价结合）。
• Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines
  作者：Brian D. Palmer、William R. Wilson、Susan M. Pullen、William A. Denny

  DOI：10.1021/jm00163a019

  日期：1990.1

  A series of aniline mustards with a wide range of electron-donating and -withdrawing substituents in the 3- and 4-positions has been synthesized and evaluated for cytotoxicity in cell culture to examine the potential of using nitro group deactivated nitrogen mustards for the design of novel hypoxia-selective anticancer drugs (Denny, W. A.; Wilson, W. R. J. Med. Chem. 1986, 29, 879). Hydrolytic half-lives in tissue culture media, determined by bioassay against a cell line (UV4) defective in the repair of DNA interstrand cross-links showed the expected dependence on the Hammett electronic parameter, sigma, varying from 0.13 h for the 4-amino analogue to greater than 100 h for analogues with strongly electron-withdrawing substituents. Cytotoxic potencies in aerobic UV4 cultures showed a similar dependence on sigma. This dependence predicted that the 4-nitroaniline mustard would be 7200-fold less potent than its potential six-electron reduction product, the 4-amino compound, in growth inhibition assays using a 1-h drug exposure. The measured differential was much lower (225-fold) because of the instability of the latter compound, but a differential of 17,500-fold was observed in the initial rate of killing by using a clonogenic assay. The potential for formation of reactive mustards by reduction to the amine or hydroxylamine was demonstrated by the 4-nitroso compound, which had an aerobic toxicity similar to that of the amine. Although these features confirmed the original rationale, the 3-nitro- and 4-nitroaniline mustards had only minimal hypoxic selectivity against UV cells. Toxicity to hypoxic cells appears to be limited by the low reduction potentials of these compounds and consequent lack of enzymatic nitroreduction. However, this study has demonstrated that nitro groups can be used to latentiate aromatic nitrogen mustards and indicates that examples with higher reduction potentials could provide useful hypoxia-selective therapeutic agents.