4-Brom-9-chlor-acridin | 4357-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-Brom-9-chlor-acridin
• 英文别名: Acridine, 4-bromo-9-chloro-；4-bromo-9-chloroacridine
• CAS: 4357-59-9
• 化学式: C₁₃H₇BrClN
• 分子量: 292.562
• InChiKey: KXSIZSPGUJHHNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氨基-N,N-二甲基苯甲酰胺 、 4-Brom-9-chlor-acridin 以92%的产率得到
  参考文献：
  名称：

  SAMARIN A. S.; STEPANOVA M. N., SB. NAUCH. TR. PERM. POLITEXN. IN-T , 1974, HO 154 75-78

  摘要：

  DOI：
• 作为产物：
  描述：

  4-bromo-9(10)acridinone 在 氯化亚砜 作用下， 生成 4-Brom-9-chlor-acridin
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Potential Anticancer Agents:  Alkylcarbamates of 3-(9-Acridinylamino)-5-hydroxymethylaniline

  摘要：

  A series of potential 9-anilinoacridine antitumor agents, 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA) derivatives with monosubstituent at C4' and disubstituents at C4' and C5' of the acridine ring and their alkylcarbamates, were synthesized for evaluation of their antitumor activity. A structure-activity relationship (SAR) study showed that the AHMA-alkylcarbamates were more potent than their corresponding parent AHMA compounds. In addition, the cytotoxicity of the AHMA-alkylcarbamate decreased with increasing length and size of the alkyl function. Among these compounds, AHMA-ethylcarbamate (18) and 4'-methyl-5'-dimethylaminoethylcarboxamido-AHMA-ethylcarbamate (34) possess potent cytotoxicity on the inhibition of human leukemic HL-60 cell growth in culture. Further in vivo studies of these compounds displayed significant anticancer therapeutic effects in mice bearing sarcoma 180, Lewis lung carcinoma, and P388 leukemia.

  DOI：

  10.1021/jm9901226

文献信息

• Potential antitumor agents. 47. 3'-Methylamino analogs of amsacrine with in vivo solid tumor activity
  作者：Graham J. Atwell、Bruce C. Baguley、Graeme J. Finlay、Gordon W. Rewcastle、William A. Denny

  DOI：10.1021/jm00159a035

  日期：1986.9

  antileukemic agent amsacrine with a 3'-methylamino group provides a compound (3) with a broader spectrum of action, including in vivo activity against experimental solid tumors. The synthesis, physicochemical properties, and biological activity of a series of acridine-substituted analogues of 3 are described. The compounds show higher levels of DNA binding, water solubility, and in vivo solid tumor activity

  用3'-甲基氨基取代临床抗白血病药物氨苯磺酸的3'-甲氧基提供了具有更广谱作用的化合物（3），包括针对实验性实体瘤的体内活性。描述了一系列3的a啶取代的类似物的合成，理化性质和生物学活性。这些化合物显示出更高的DNA结合水平，水溶性和体内实体瘤活性（刘易斯肺癌），而其氨色林对应物更高。然而，a啶取代的结构-活性关系是不同的，其中3,5-二取代的3'-甲基氨基化合物显示出最高的活性（与4,5-二取代的氨ac碱类似物相比）。
• ATWELL G. J.; BAGULEY B. C.; FINLAY G. J.; REWCASTLE G. W.; DENNY W. A., J. MED. CHEM., 29,(1986) N 9, 1769-1776
  作者：ATWELL G. J.、 BAGULEY B. C.、 FINLAY G. J.、 REWCASTLE G. W.、 DENNY W. A.

  DOI：——

  日期：——
• Synthesis and Structure−Activity Relationships of Potential Anticancer Agents:  Alkylcarbamates of 3-(9-Acridinylamino)-5-hydroxymethylaniline
  作者：Tsann-Long Su、Ching-Huang Chen、Lin-Fei Huang、Chao-Hao Chen、Manas K. Basu、Xiu-Guo Zhang、Ting-Chao Chou

  DOI：10.1021/jm9901226

  日期：1999.11.1

  A series of potential 9-anilinoacridine antitumor agents, 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA) derivatives with monosubstituent at C4' and disubstituents at C4' and C5' of the acridine ring and their alkylcarbamates, were synthesized for evaluation of their antitumor activity. A structure-activity relationship (SAR) study showed that the AHMA-alkylcarbamates were more potent than their corresponding parent AHMA compounds. In addition, the cytotoxicity of the AHMA-alkylcarbamate decreased with increasing length and size of the alkyl function. Among these compounds, AHMA-ethylcarbamate (18) and 4'-methyl-5'-dimethylaminoethylcarboxamido-AHMA-ethylcarbamate (34) possess potent cytotoxicity on the inhibition of human leukemic HL-60 cell growth in culture. Further in vivo studies of these compounds displayed significant anticancer therapeutic effects in mice bearing sarcoma 180, Lewis lung carcinoma, and P388 leukemia.
• SAMARIN A. S.; STEPANOVA M. N., SB. NAUCH. TR. PERM. POLITEXN. IN-T <NTRR-AU>, 1974, HO 154 75-78
  作者：SAMARIN A. S.、 STEPANOVA M. N.

  DOI：——

  日期：——