3-[双(2-氯乙基)氨基]-4-甲基苯甲酸 | 5977-35-5

• 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: 3-[双(2-氯乙基)氨基]-4-甲基苯甲酸
• 英文名称: 4-methyl-3,3-N,N-bis(2-chloroethyl)aminobenzoic acid
• 英文别名: p-methyl-m-N,N-bis(2-chloroethyl)aminobenzoic acid；3-(N,N-Bis-<2-chlor-ethyl>-amino)-4-methyl-benzoesaeure；4-Methyl-3benzoesaeure；3-Diaethylchloramino-4-methyl-benzoesaeure；3-Di-(2-chlor-ethyl)-amino-4-tolusaeure；3-[Bis(2-chloroethyl)amino]-4-methylbenzoic acid
• CAS: 5977-35-5
• 化学式: C₁₂H₁₅Cl₂NO₂
• 分子量: 276.163
• InChiKey: DKROWFJGHDLNFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  125°C (rough estimate)
• 密度：
  1.2884 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

制备方法与用途

类别：有毒物品

毒性分级：剧毒

急性毒性：

• 腹腔-大鼠 LD50: 17 毫克/公斤

可燃性危险特性：

• 可燃；燃烧时产生有毒氮氧化物和氯化物烟雾

储运特性：

• 库房应保持通风、低温和干燥
• 与食品原料分开存放

灭火剂：

• 干粉、泡沫、砂土、二氧化碳
• 雾状水

反应信息

• 作为反应物：
  描述：

  3-[双(2-氯乙基)氨基]-4-甲基苯甲酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 3-[双(2-氯乙基)氨基]-4-甲基苯甲酰氯
  参考文献：
  名称：

  N，N-双（2-氯乙基）氨基苯甲酸异构体的均氮氮类甾醇酯的形成及其抗肿瘤活性

  摘要：

  3 ， β-羟基-13α-氨基-13,17-seco-5α的N，N-双（2-氯乙基）氨基苯甲酸酯异构体和4-甲基-3 - N，N-双（2-氯乙基）氨基苯甲酸酯-androstan-17-oic-13,17-内酰胺，3α-羟基-13α-氨基-13,17-seco-5α-androstan-17-oic-13,17-内酰胺，3α-羟基-13α-氨基-13制备了1,17-seco-5-androsten-17-oic-13,17-内酰胺和17β-羟基-3-氮杂-A-homo-4α-androsten-4-one，并评估了其对P388白血病的生物学活性体内和艾氏腹水肿瘤（EAT），P388和L1210白血病以及体外婴儿仓鼠细胞（BHK）。在P388白血病中，烷基化同源物在轴向位置与内酰胺醇连接的酯在体内无活性，而化合物1，4，6，13，14和所述烷基化同类物17，18和20是活动的。N，N-双（2

  DOI：

  10.1002/jhet.5570310219

文献信息

• Rational design, synthesis, and in vivo evaluation of the antileukemic activity of six new alkylating steroidal esters
  作者：Anna I. Koutsourea、Manolis A. Fousteris、Evagelia S. Arsenou、Athanasios Papageorgiou、George N. Pairas、Sotiris S. Nikolaropoulos

  DOI：10.1016/j.bmc.2008.03.015

  日期：2008.5

  The synthesis and the in vivo evaluation against leukemias P388 and L1210 of six new alkylating steroidal esters are described. The esteric derivatives incorporating the 17 beta-acetamido-B-lactamic steroidal skeleton exhibited increased antileukemic activity and lower toxicity, compared to the 17 beta-acetamido-7-keto analogs. Among the 17 beta-acetamido-B-lactamic steroidal esters, the most potent compound afforded four out of six cures in leukemia P388 and was measured to be almost non-toxic, producing significant low levels of toxicity. (C) 2008 Elsevier Ltd. All rights reserved.
• A new approach for evaluating in vivo anti-leukemic activity using the SCE assay
  作者：Venetia Karayianni、Eleftheria Mioglou、Zafiroula Iakovidou、Dionysios Mourelatos、Manolis Fousteris、Anna Koutsourea、Evaggelia Arsenou、Sotiris Nikolaropoulos

  DOI：10.1016/s1383-5718(02)00286-3

  日期：2003.2

  Three newly synthesised steroidal esteric derivatives of nitrogen mustard (compounds 1-3) were comparatively studied on a molar basis regarding their ability to induce sister chromatid exchanges (SCEs) in normal human lymphocytes in vitro and therapeutic effects on leukemia P388 bearing mice. Compounds 1 and 3 are modified steroidal esters of p-methyl-m-N,N-bis(2-chloroethyl)amino benzoic acid, and compound 2 is a modified steroidal ester of chlorambucil. All compounds induced statistically significant increases in SCEs and decreases in proliferation rate indices (PRIs) of cultured human lymphocytes and significantly increased the life span of P388 bearing mice. In this study, the doses applied for therapeutic purposes upon leukemia P388 bearing mice in vivo were derived from cytogenetic observations in normal human lymphocytes in vitro. A substantially better therapeutic effect was obtained compared to the effect achieved after the use of quite higher doses related with LD10 values. We have demonstrated that the order of anti-tumour effectiveness of the treatment schedules of the three newly synthesised compounds tested (at doses derived from cytogenetic observations) coincides with the order of the cytogenetic effects they induce. The SCE assay appears to have an application in the clinical prediction of tumour sensitivity to potential chemotherapeutics. (C) 2002 Elsevier Science B.V. All rights reserved.
• NICULESCU-DUVAZ I.; TOMA A.; ROTARU M.; IONESCU D.; BARACU I.; BOTEZ G.; +, REV. ROUM. CHIM., 1979, 24, NO 4, 583-596
  作者：NICULESCU-DUVAZ I.、 TOMA A.、 ROTARU M.、 IONESCU D.、 BARACU I.、 BOTEZ G.、 +

  DOI：——

  日期：——
• DUVAZ, I. M. C. N.;ELIAN, I.;DOBRE, V.
  作者：DUVAZ, I. M. C. N.、ELIAN, I.、DOBRE, V.

  DOI：——

  日期：——
• ESTERS OF STEROIDAL LACTAM AND BIS(2-CHLOROETHYL) AMINOPHENOXY PROPANOIC ACID DERIVATIVES
  申请人：Galenica S.A.

  公开号：EP3186268B1

  公开（公告）日：2018-11-28