1-(4-氯-3-硝基苯基)-1-丙酮 | 80093-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-氯-3-硝基苯基)-1-丙酮
• 英文名称: (4-Chlor-3-nitrophenyl)-ethylketon
• 英文别名: 4-Chlor-3-nitro-propiophenon；1-(4-chloro-3-nitro-phenyl)-propan-1-one；1-(4-Chlor-3-nitro-phenyl)-propan-1-on；1-(4-Chloro-3-nitrophenyl)propan-1-one
• CAS: 80093-43-2
• 化学式: C₉H₈ClNO₃
• mdl: MFCD08437181
• 分子量: 213.62
• InChiKey: OGEKZGZVHGKFGG-UHFFFAOYSA-N

物化性质

• 熔点：
  61 °C
• 沸点：
  302.5±22.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-氯-3-硝基苯基)-1-丙酮 在 氨 作用下， 生成 1-(4-氨基-3-硝基苯基)丙烷-1-酮
  参考文献：
  名称：

  Raeymackers; Van Gelder; Roevens, Arzneimittel-Forschung/Drug Research, 1978, vol. 28, # 4, p. 586 - 594

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯丙酮 在 硫酸 、 硝酸 作用下， 反应 0.25h， 以10%的产率得到1-(4-氯-3-硝基苯基)-1-丙酮
  参考文献：
  名称：

  Syntheses andIn VitroAnticancer Properties of Novel Radiosensitizers

  摘要：

  Series of 4‐(ethylsulfonyl)‐1‐halogen‐2‐nitrobenzene (3a–e) and 1‐(4‐halogen‐3‐nitrophenyl) propan‐1‐one (5a–d) analogs designed as novel radiosensitizers using bromonitropropiophenone and bromonitrobenzonitrile as lead compounds were synthesized. The anticancer activities of the compounds were evaluated in vitro using human prostate cancer (DU‐145) and breast cancer (MCF‐7) cell lines and the MTT assay. From the series, six compounds (3b–e, 5b–c) exhibited potent growth inhibitory effects against both cell lines. The most active, compound 3d, is an iodosulfone and is significantly more potent than the lead compound 5c at 10 μm. Compounds were then compared with doxorubicin, a clinically used anticancer compound for breast and prostate cancers. Our most active compound 3d is more effective than doxorubicin at the dose level of 10 μm at 3 days after radiation, cell viabilities of 18%, 13% compared to 87%, 94% against MCF‐7, and 15%, 20% compared to 60%, 75% against DU‐145 without and with radiation, respectively. At 10 μm, compound 5c had no effects as compared to control, whereas compound 3d reduced DU‐145 cell viability to 16% and that of MCF‐7 cells to 9% even at 5 days after radiation. These results are very encouraging. Future studies include testing the compounds in vivo with and without radiation.

  DOI：

  10.1111/j.1747-0285.2012.01442.x

文献信息

• Addition of Grignard Reagents to Aryl Acid Chlorides:  An Efficient Synthesis of Aryl Ketones
  作者：Xiao-jun Wang、Li Zhang、Xiufeng Sun、Yibo Xu、Dhileepkumar Krishnamurthy、Chris H. Senanayake

  DOI：10.1021/ol052150q

  日期：2005.12.1

  addition of Grignard reagents to acid chlorides in the presence of bis[2-(N,N-dimethylamino)ethyl] ether proceeds selectively to provide aryl ketones in high yields. A possible tridentate interaction between Grignard reagents and bis[2-(N,N-dimethylamino)ethyl] ether moderates the reactivity of Grignard reagents, preventing the newly formed ketones from nucleophilic addition by Grignard reagents.

  [化学反应：见正文]。在双[2-（N，N-二甲基氨基）乙基]醚存在下，将格氏试剂直接添加到酰氯中选择性地进行，以高收率提供芳基酮。格氏试剂与双[2-（N，N-二甲基氨基）乙基]醚之间可能的三齿相互作用会减缓格氏试剂的反应性，从而防止新形成的酮被格氏试剂亲核加成。
• Novel Compounds for Treatment of Malignant Tumors
  申请人：Koumenis Constantinos

  公开号：US20110190400A1

  公开（公告）日：2011-08-04

  The present invention comprises compounds, compositions and methods of use for sensitizing cancer cells, tumors, neoplasms, and malignancies to the effects of ionizing radiation used in the treatment of cancer. The invention further comprises a method of identifying novel radiosensitizing compounds.

  本发明涉及化合物、组合物和使用方法，用于增敏癌细胞、肿瘤、新生物和恶性肿瘤对用于治疗癌症的电离辐射的影响。本发明还涉及一种识别新的放射增敏化合物的方法。
• Oelschlaeger,H.; Schreiber,O., Justus Liebigs Annalen der Chemie, 1961, vol. 641, p. 81 - 94
  作者：Oelschlaeger,H.、Schreiber,O.

  DOI：——

  日期：——
• Über lokalanästhesierende α-Amino-3-alkyl-acetanilide Mitt. über Synthesen neuer Verbindungen mit lokalanästhetischer Wirkung)
  作者：Herbert Oelschläger

  DOI：10.1002/ardp.19572901204

  日期：——
• AGAFONOV, I. E.;SEDISHEV, I. I.;DUDIN, A. V.;KUTIN, A. A.;STASHINA, G. A.+, IZV. AN CCCP. CEP. XIM.,(1991) N, S. 426-433
  作者：AGAFONOV, I. E.、SEDISHEV, I. I.、DUDIN, A. V.、KUTIN, A. A.、STASHINA, G. A.+

  DOI：——

  日期：——