4-nitrophenyl 4'-phenyl sulfide | 133041-83-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-nitrophenyl 4'-phenyl sulfide
• 英文别名: N,N-bis-(2-chloroethyl)-4-(4-nitrophenylthio)aniline；Benzenamine, N,N-bis(2-chloroethyl)-4-[(4-nitrophenyl)thio]-；N,N-bis(2-chloroethyl)-4-(4-nitrophenyl)sulfanylaniline
• CAS: 133041-83-5
• 化学式: C₁₆H₁₆Cl₂N₂O₂S
• 分子量: 371.287
• InChiKey: AIACGJOEAGBUBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 4'-phenyl sulfide 在 盐酸 、 铁粉 作用下， 以 N-甲基吡咯烷酮 、 乙醇 为溶剂， 反应 1.75h， 生成 N-[4-[4-[bis(2-chloroethyl)amino]phenyl]sulfanylphenyl]acridin-9-amine;hydrochloride
  参考文献：
  名称：

  Sulfoxide-Containing Aromatic Nitrogen Mustards as Hypoxia-Directed Bioreductive Cytotoxins

  摘要：

  A series of diaryl and alkylaryl sulfoxide-containing nitrogen mustards were synthesized and evaluated for their hypoxia-selective cytotoxicity against V-79 cells in vitro as well as for their metabolism profiles with the rat S-9 fractions. In general, the diaryl sulfoxides (4, 5, and 7-9) showed much greater hypoxia selectivity (11-27-fold) than the alkylaryl sulfoxides (similar to3-fold) (1 and 3). The fused diphenyl sulfoxides (10 and 11), on the other hand, showed very low hypoxia selectivity (1.3-3-fold). Compound 10 was highly cytotoxic under both aerobic and anaerobic conditions, while 11 showed low cytotoxicity under both conditions. The bioreduction of 8 by the rat S-9 fraction under anaerobic conditions was inhibited by menadione and enhanced by benzaldehyde, acetaldehyde, or 2-hydroxypyrimidine suggesting the involvement of aldehyde oxidase in the reduction of the sulfoxides. Bioreductive metabolism studies of selected model sulfoxides suggested that diaryl sulfoxides are better substrates for aldehyde oxidase than alkylaryl sulfoxides.

  DOI：

  10.1021/jm9904957
• 作为产物：
  描述：

  4-nitrophenyl 4'-phenyl sulfide 在 三氯氧磷 作用下， 反应 0.67h， 以80.2%的产率得到4-nitrophenyl 4'-phenyl sulfide
  参考文献：
  名称：

  Sulfoxide-Containing Aromatic Nitrogen Mustards as Hypoxia-Directed Bioreductive Cytotoxins

  摘要：

  A series of diaryl and alkylaryl sulfoxide-containing nitrogen mustards were synthesized and evaluated for their hypoxia-selective cytotoxicity against V-79 cells in vitro as well as for their metabolism profiles with the rat S-9 fractions. In general, the diaryl sulfoxides (4, 5, and 7-9) showed much greater hypoxia selectivity (11-27-fold) than the alkylaryl sulfoxides (similar to3-fold) (1 and 3). The fused diphenyl sulfoxides (10 and 11), on the other hand, showed very low hypoxia selectivity (1.3-3-fold). Compound 10 was highly cytotoxic under both aerobic and anaerobic conditions, while 11 showed low cytotoxicity under both conditions. The bioreduction of 8 by the rat S-9 fraction under anaerobic conditions was inhibited by menadione and enhanced by benzaldehyde, acetaldehyde, or 2-hydroxypyrimidine suggesting the involvement of aldehyde oxidase in the reduction of the sulfoxides. Bioreductive metabolism studies of selected model sulfoxides suggested that diaryl sulfoxides are better substrates for aldehyde oxidase than alkylaryl sulfoxides.

  DOI：

  10.1021/jm9904957

文献信息

• F-18 labelledN,N-bis-haloethylamino-phenylsulfoxides — a new class of compounds for the imaging of hypoxic tissue
  作者：Cheryl L. Falzon、Uwe Ackermann、Neil Spratt、Henri J. Tochon-Danguy、Jonathon White、David Howells、Andrew M. Scott

  DOI：10.1002/jlcr.1129

  日期：2006.10.30

  Two N,N-bis-chloroethylamino-phenylsulfoxides have been synthesized and radiolabelled with F-18 via halogen exchange. The radiolabelling of both compounds proceeds smoothly with K[18F]F-kryptofix 2.2.2 complex at 100 °C in DMSO. Decay-corrected radiochemical yields were 25–35% for [18F]12 (SO201) and 35–45% for [18F]11 (SO101), with an average specific activity of 1.8 Ci/µmol. Both compounds remained 80% intact in plasma over a period of 2 h. In vivo binding in a stroke model indicates that both markers are selectively retained in hypoxic tissue. Copyright © 2006 John Wiley & Sons, Ltd.

  我们合成了两种 N,N-双氯乙基氨基苯基硫氧化物，并通过卤素交换用 F-18 进行了放射性标记。在 100 °C 的二甲基亚砜中，这两种化合物与 K[18F]F-kryptofix 2.2.2 复合物一起顺利进行放射性标记。衰变校正放射化学产率为：[18F]12 (SO201) 25-35%，[18F]11 (SO101)35-45%，平均比活度为 1.8 Ci/µmol。在中风模型中的体内结合表明，这两种标记物都能选择性地保留在缺氧组织中。Copyright © 2006 John Wiley & Sons, Ltd. All Rights Reserved.
• DNA-directed alkylating agents. 4. 4-Anilinoquinoline-based minor groove directed aniline mustards
  作者：G. Lance Gravatt、Bruce C. Baguley、William R. Wilson、William A. Denny

  DOI：10.1021/jm00109a005

  日期：1991.5

  A series of 4-anilinoquinoline-linked aniline mustards of widely varying mustard reactivity were prepared and evaluated for their antitumor activity. The compounds were designed as minor groove binding agents, where the aniline mustard ring is itself part of the DNA-binding ligand. While there was a general trend for cytotoxicity to correlate with mustard reactivity, this was much less pronounced than with untargeted mustards. The compounds were much more cytotoxic than the parent diols, and were at least 10-fold more cytotoxic than the corresponding aniline mustards themselves. Comparative cell line studies suggested that the mechanism of cytotoxicity varied with mustard reactivity. The most reactive mustards cross-linked DNA, while cell killing by the less reactive compounds appeared to be by the formation of bulky monoadducts. The compounds were active but not particularly dose-potent against P388 leukemia in vivo. The modest potency may be related to their poor aqueous solubility, since the more soluble methyl quaternary salts were equally active at much lower doses.
• GRAVATT, G. LANCE;BAGULEY, BRUCE C.;WILSON, WILLIAM R.;DENNY, WILLIAM A., J. MED. CHEM., 34,(1991) N, C. 1552-1560
  作者：GRAVATT, G. LANCE、BAGULEY, BRUCE C.、WILSON, WILLIAM R.、DENNY, WILLIAM A.

  DOI：——

  日期：——
• Sulfoxide-Containing Aromatic Nitrogen Mustards as Hypoxia-Directed Bioreductive Cytotoxins
  作者：Zhong-Yue Sun、Emad Botros、Ai-Duen Su、Yu Kim、Enju Wang、Nesrine Z. Baturay、Chul-Hoon Kwon

  DOI：10.1021/jm9904957

  日期：2000.11.1

  A series of diaryl and alkylaryl sulfoxide-containing nitrogen mustards were synthesized and evaluated for their hypoxia-selective cytotoxicity against V-79 cells in vitro as well as for their metabolism profiles with the rat S-9 fractions. In general, the diaryl sulfoxides (4, 5, and 7-9) showed much greater hypoxia selectivity (11-27-fold) than the alkylaryl sulfoxides (similar to3-fold) (1 and 3). The fused diphenyl sulfoxides (10 and 11), on the other hand, showed very low hypoxia selectivity (1.3-3-fold). Compound 10 was highly cytotoxic under both aerobic and anaerobic conditions, while 11 showed low cytotoxicity under both conditions. The bioreduction of 8 by the rat S-9 fraction under anaerobic conditions was inhibited by menadione and enhanced by benzaldehyde, acetaldehyde, or 2-hydroxypyrimidine suggesting the involvement of aldehyde oxidase in the reduction of the sulfoxides. Bioreductive metabolism studies of selected model sulfoxides suggested that diaryl sulfoxides are better substrates for aldehyde oxidase than alkylaryl sulfoxides.