1-(5-phenylsulfanyl-4-nitro-2-thienyl)ethanone | 90680-28-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(5-phenylsulfanyl-4-nitro-2-thienyl)ethanone
• 英文别名: 1-(5-Phenylsulfanyl-4-nitro-2-thienyl)ethanone；1-(4-nitro-5-phenylsulfanylthiophen-2-yl)ethanone
• CAS: 90680-28-7
• 化学式: C₁₂H₉NO₃S₂
• mdl: MFCD25924251
• 分子量: 279.34
• InChiKey: WZNUDHSRSDPPHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  422.8±45.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙酰基-5-氯噻酚 在 硝酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-(5-phenylsulfanyl-4-nitro-2-thienyl)ethanone
  参考文献：
  名称：

  Selective Dual Inhibitors of the Cancer-Related Deubiquitylating Proteases USP7 and USP47

  摘要：

  Inhibitors of the cancer-related cysteine isopeptidase human ubiquitin-specific proteases 7 (USP7) and 47 (USP47) are considered to have potential as cancer therapeutics, owing to their ability to stabilize the tumor suppressor p53 and to decrease DNA polymerase beta (Pol beta), both of which are potential anticancer effects. A new class of dual small molecule inhibitors of these enzymes has been discovered. Compound 1, a selective inhibitor of USP7 and USP47 with moderate potency, demonstrates inhibition of USP7 in cells and induces elevated p53 and apoptosis in cancer cell lines. Compound 1 has been shown to demonstrate modest activity in human xenograft multiple myeloma and B-cell leukemia in vivo models. This activity may be the result of dual inhibition of USP7 and USP47. To address issues regarding potency and developability, analogues of compound 1 have been synthesized and tested, leading to improvements in potency, solubility, and metabolic reactivity profile. Further optimization is expected to yield preclinical candidates and, ultimately, clinical candidates for the treatment of multiple myeloma, prostate cancer, and other cancers.

  DOI：

  10.1021/ml200276j

文献信息

• Noto, Renato; Frenna, Vincenzo; Consiglio, Giovanni, Journal of Chemical Research, Miniprint, 1991, # 10, p. 2701 - 2710
  作者：Noto, Renato、Frenna, Vincenzo、Consiglio, Giovanni、Spinelli, Domenico

  DOI：——

  日期：——
• Selective Dual Inhibitors of the Cancer-Related Deubiquitylating Proteases USP7 and USP47
  作者：Joseph Weinstock、Jian Wu、Ping Cao、William D. Kingsbury、Jeffrey L. McDermott、Matthew P. Kodrasov、Devin M. McKelvey、K. G. Suresh Kumar、Seth J. Goldenberg、Michael R. Mattern、Benjamin Nicholson

  DOI：10.1021/ml200276j

  日期：2012.10.11

  Inhibitors of the cancer-related cysteine isopeptidase human ubiquitin-specific proteases 7 (USP7) and 47 (USP47) are considered to have potential as cancer therapeutics, owing to their ability to stabilize the tumor suppressor p53 and to decrease DNA polymerase beta (Pol beta), both of which are potential anticancer effects. A new class of dual small molecule inhibitors of these enzymes has been discovered. Compound 1, a selective inhibitor of USP7 and USP47 with moderate potency, demonstrates inhibition of USP7 in cells and induces elevated p53 and apoptosis in cancer cell lines. Compound 1 has been shown to demonstrate modest activity in human xenograft multiple myeloma and B-cell leukemia in vivo models. This activity may be the result of dual inhibition of USP7 and USP47. To address issues regarding potency and developability, analogues of compound 1 have been synthesized and tested, leading to improvements in potency, solubility, and metabolic reactivity profile. Further optimization is expected to yield preclinical candidates and, ultimately, clinical candidates for the treatment of multiple myeloma, prostate cancer, and other cancers.