吡咯烷,1-[(2-碘苯基)偶氮]- | 188966-38-3

• 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: 吡咯烷,1-[(2-碘苯基)偶氮]-
• 英文名称: 1-[(2-iodophenyl)diazenyl]pyrrolidine
• 英文别名: (2-Iodophenyl)-pyrrolidin-1-yldiazene
• CAS: 188966-38-3
• 化学式: C₁₀H₁₂IN₃
• 分子量: 301.13
• InChiKey: LHHKBNMXCCYHSM-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  341.6±44.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  28
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡咯烷,1-[(2-碘苯基)偶氮]- 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 碘甲烷 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 triisopropyl((2-((2-((2-((triisopropylsilyl)ethynyl)phenyl)buta-1,3-diyn-1-yl)phenyl)hexa-1,3,5-triyn-1-yl)phenyl)ethynyl)silane
  参考文献：
  名称：

  Synthesis of expanded planar dehydrobenzoannulenes: Weakly diatropic, weakly paratropic, or atropic?

  摘要：

  Use of a Cu/Pd cross-coupling strategy has led to the synthesis of the first dehydrobenzoannulenes containing triacetylenic linkages. NMR studies of these macrocycles and comparison with other known systems indicate that, in spite of their large size and extensive benzannelation, dehydrobenzoannulenes possess weak induced ring currents. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01583-4
• 作为产物：
  描述：

  四氢吡咯 、 2-碘苯胺 在 盐酸 、 水 、 sodium nitrite 作用下， 生成 吡咯烷,1-[(2-碘苯基)偶氮]-
  参考文献：
  名称：

  NEW SYNTHESIS OF PHENYLTHIOGLYCOLIC ACIDSviaRELATED TRIAZENE COMPOUNDS

  摘要：

  DOI：

  10.1080/00304949809355295

文献信息

• New Synthetic Technology for the Synthesis of Aryl Ethers:  Construction of C-O-D and D-O-E Ring Model Systems of Vancomycin
  作者：K. C. Nicolaou、C. N. C. Boddy、S. Natarajan、T.-Y. Yue、H. Li、S. Bräse、J. M. Ramanjulu

  DOI：10.1021/ja9636350

  日期：1997.4.1
• A novel organobismuth compound, 1-[(2-di-p-tolylbismuthanophenyl)diazenyl]pyrrolidine, induces apoptosis in the human acute promyelocytic leukemia cell line NB4 via reactive oxygen species
  作者：Kengo Onishi、Mizuho Douke、Taisuke Nakamura、Youta Ochiai、Naoki Kakusawa、Shuji Yasuike、Jyoji Kurita、Chika Yamamoto、Masatoshi Kawahata、Kentaro Yamaguchi、Tatsuo Yagura

  DOI：10.1016/j.jinorgbio.2012.09.009

  日期：2012.12

  A novel organobismuth compound, 1-[(2-di-p-tolylbismuthanophenyl)diazenyl]pyrrolidine (4), which has 1-(phenyldiazenyl)pyrrolidine (1) substituent in a benzene ring of tri(p-tolyl)bismuthane (2), was synthesized and tested for biological activity toward human tumor cell lines. 4 had a potent anti-proliferative effect on human cancer cell lines, although both 1 and 2 exhibited only weak activity. The sensitivity of leukemic cell lines to 4 was relatively high; IC50 values for the human leukemia cell line NB4 and cervical cancer cell line HeLa were 0.88 mu M and 5.36 mu M, respectively. Treatment of NB4 cells with 4 induced apoptosis, loss of mitochondrial membrane potential (Delta psi(mt)) and the generation of cellular reactive oxygen species (ROS). 1 and 2 did not induce apoptosis and had only a marginal effect on Delta psi(mt) and the generation of ROS. N-acetyl cysteine (NAC) reduced the generation of ROS and conferred protection against 4-induced apoptosis, indicating a role for oxidative stress. 4 did not inhibit the polymerization of tubulin in vitro. 1-[2-(di-p-tolylstibanophenyl)diazenyl]pyrrolidine (3), which has the same chemical structure as 4 but contains antimony in place of bismuth, did not show any cytotoxic activity. The results suggest that the conjugated structure of the diazenylpyrrolidine moiety and bismuth center are key to the bioactivity of 4. (C) 2012 Elsevier Inc. All rights reserved.