5-iodo-N-chloroacetylanthranilic acid | 175850-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-iodo-N-chloroacetylanthranilic acid
• 英文别名: 2'-Carboxy-2-chloro-4'-iodoacetanilide；2-[(2-chloroacetyl)amino]-5-iodobenzoic acid
• CAS: 175850-45-0
• 化学式: C₉H₇ClINO₃
• mdl: MFCD00029967
• 分子量: 339.517
• InChiKey: WTVIFCWXMXHVSE-UHFFFAOYSA-N

物化性质

• 沸点：
  503.0±50.0 °C(Predicted)
• 密度：
  2.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-iodo-N-chloroacetylanthranilic acid 在 乙酸酐 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  El-Hakim, A. E.; Abdel-Hamid, S. G., Egyptian Journal of Chemistry, 1996, vol. 39, # 4, p. 387 - 393

  摘要：

  DOI：
• 作为产物：
  描述：

  氯乙酰氯 、 2-氨基-5-碘苯甲酸 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到5-iodo-N-chloroacetylanthranilic acid
  参考文献：
  名称：

  El-Hakim, A. E.; Abdel-Hamid, S. G., Egyptian Journal of Chemistry, 1996, vol. 39, # 4, p. 387 - 393

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of quinazolin-4-ones as hypoxia-inducible factor-1α inhibitors
  作者：Wenwei Huang、Ruili Huang、Matias S. Attene-Ramos、Srilatha Sakamuru、Erika E. Englund、James Inglese、Christopher P. Austin、Menghang Xia

  DOI：10.1016/j.bmcl.2011.07.043

  日期：2011.9

  Quinazolin-4-one 1 was identified as an inhibitor of the HIF-1 alpha transcriptional factor from a high-throughput screen. HIF-1 alpha up-regulation is common in many cancer cells. In this Letter, we describe an efficient one-pot sequential reaction for the synthesis of quinazolin-4-one 1 analogues. The structure-activity relationship (SAR) study led to the 5-fold more potent analogue, 16. Published by Elsevier Ltd.
• Development of (<i>E</i>)-2-((1,4-Dimethylpiperazin-2-ylidene)amino)-5-nitro-<i>N</i>-phenylbenzamide, ML336: Novel 2-Amidinophenylbenzamides as Potent Inhibitors of Venezuelan Equine Encephalitis Virus
  作者：Chad E. Schroeder、Tuanli Yao、Julie Sotsky、Robert A. Smith、Sudeshna Roy、Yong-Kyu Chu、Haixun Guo、Nichole A. Tower、James W. Noah、Sara McKellip、Melinda Sosa、Lynn Rasmussen、Layton H. Smith、E. Lucile White、Jeffrey Aubé、Colleen B. Jonsson、Donghoon Chung、Jennifer E. Golden

  DOI：10.1021/jm501203v

  日期：2014.10.23

  Venezuelan equine encephalitis virus (VEEV) is an emerging pathogenic alphavirus that can cause significant disease in humans. Given the absence of therapeutic options available and the significance of VEEV as a weaponized agent, an optimization effort was initiated around a quinazolinone screening hit 1 with promising cellular antiviral activity (EC50 = 0.8 mu M), limited cytotoxic liability (CC50 > 50 mu M), and modest in vitro efficacy in reducing viral progeny (63-fold at 5 mu M). Scaffold optimization revealed a novel rearrangement affording amidines, specifically compound 45, which was found to potently inhibit several VEEV strains in the low nanomolar range without cytotoxicity (EC50 = 0.02-0.04 mu M, CC50 > 50 mu M) while limiting in vitro viral replication (EC90 = 0.17 mu M). Brain exposure was observed in mice with 45. Significant protection was observed in VEEV-infected mice at 5 mg kg(-1) day(-1) and viral replication appeared to be inhibited through interference of viral nonstructural proteins.
• El-Hakim, A. E.; Abdel-Hamid, S. G., Egyptian Journal of Chemistry, 1996, vol. 39, # 4, p. 387 - 393
  作者：El-Hakim, A. E.、Abdel-Hamid, S. G.

  DOI：——

  日期：——