6-chloro-1,3-benzoxazole-2-carbonitrile | 1172606-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 6-chloro-1,3-benzoxazole-2-carbonitrile
• 英文别名: 6-chlorobenzo[d]oxazole-2-carbonitrile；6-Chloro-1,3-benzoxazole-2-carbonitrile
• CAS: 1172606-59-5
• 化学式: C₈H₃ClN₂O
• 分子量: 178.578
• InChiKey: WRGAPTQLONVIEY-UHFFFAOYSA-N

物化性质

• 沸点：
  302.2±34.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-1,3-benzoxazole-2-carbonitrile 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 6-chloro-N'-hydroxy-1,3-benzoxazole-2-carboximidamide
  参考文献：
  名称：

  Chloro-oxime derivatives as novel small molecule chaperone amplifiers

  摘要：

  Chloro-oxime derivatives were investigated as novel small molecule chaperone amplifiers. Lead optimization led to the discovery of compounds that displayed potent HSF1 activation activity, significant cytoprotection in MG-132 stress, ER stress and PolyQ stress cell models (EC50 < 10 mu M). (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.011
• 作为产物：
  描述：

  6-chlorobenzo[d]oxazole-2-carbaldehyde oxime 在 氯化亚砜 作用下， 反应 1.0h， 生成 6-chloro-1,3-benzoxazole-2-carbonitrile
  参考文献：
  名称：

  Chloro-oxime derivatives as novel small molecule chaperone amplifiers

  摘要：

  Chloro-oxime derivatives were investigated as novel small molecule chaperone amplifiers. Lead optimization led to the discovery of compounds that displayed potent HSF1 activation activity, significant cytoprotection in MG-132 stress, ER stress and PolyQ stress cell models (EC50 < 10 mu M). (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.011

文献信息

• Discovery of selective fragment-sized immunoproteasome inhibitors
  作者：Levente Kollár、Martina Gobec、Bence Szilágyi、Matic Proj、Damijan Knez、Péter Ábrányi-Balogh、László Petri、Tímea Imre、Dávid Bajusz、György G. Ferenczy、Stanislav Gobec、György M. Keserű、Izidor Sosič

  DOI：10.1016/j.ejmech.2021.113455

  日期：2021.7

  benzoXazole-2(3H)-thiones) as inhibitors of the chymotrypsin-like (β5i) subunit of the immunoproteasome. A subsequent structure-activity relationship study provided us with an insight regarding growing vectors. Binding to the β5i subunit was shown and selectivity against the β5 subunit of the constitutive proteasome was determined. Thorough characterization of these compounds suggested that they inhibit the immunoproteasome

  蛋白酶体有助于维持蛋白质稳态，其抑制作用对某些类型的癌症和自身免疫疾病有益。然而，对健康细胞中蛋白酶体的抑制会导致不希望有的副作用，并且已经做出重大努力来鉴定对免疫蛋白酶体具有特异性的抑制剂，特别是用于治疗表现出该蛋白酶体同种型的水平和活性增加的疾病。在这里，我们报告了我们为发现人类免疫蛋白酶体的片段大小抑制剂所做的努力。内部结构多样化片段文库的筛选导致苯并[ d ]恶唑-2(3 H )-硫酮、苯并[ d ]噻唑-2(3 H )-硫酮、苯并[ d ]恶唑-2(3 H )-硫酮的鉴定]咪唑-2(3 H )-硫酮和 1-甲基苯并[ d ]咪唑-2(3 H )-硫酮（通用术语苯并恶唑-2（3 H）)-硫酮) 作为免疫蛋白酶体胰凝乳蛋白酶样 (β5i) 亚基的抑制剂。随后的构效关系研究为我们提供了有关生长载体的见解。显示了与 β5i 亚基的结合，并确定了对组成型蛋白酶体的 β5 亚基的选择性。对这些化合物的彻底表征表明，它们通过与
• Direct Transformation of Nitrogen-Containing Methylheteroarenes to Heteroaryl Nitrile by Sodium Nitrite
  作者：Chenhui Jiang、Yuqin Chen、Pan Gao、Shuwei Zhang、Xiaodong Jia、Yu Yuan

  DOI：10.1021/acs.orglett.2c02596

  日期：2022.9.2

  The cyanation reaction of methylheteroarenes with acetyl chloride and sodium nitrite via the radical process in high yields is reported. According to the control experiments, the reaction mechanism underwent radical progress. It is very useful in the pharmacy industry due to its metal-free and easy treatment conditions.

  报道了甲基杂芳烃与乙酰氯和亚硝酸钠通过自由基过程以高收率进行的氰化反应。根据对照实验，反应机理发生了根本性的进展。由于其不含金属且易于处理的条件，它在制药行业非常有用。
• Chloro-oxime derivatives as novel small molecule chaperone amplifiers
  作者：Yuefen Zhou、Khang Vu、Yongsheng Chen、John Pham、Thomas Brady、Gang Liu、Jinhua Chen、Joonwoo Nam、P.S. Murali Mohan Reddy、Qingyan Au、Il Sang Yoon、Marie-Helene Tremblay、Gary Yip、Charmian Cher、Bin Zhang、Jack R. Barber、Shi Chung Ng

  DOI：10.1016/j.bmcl.2009.03.011

  日期：2009.6

  Chloro-oxime derivatives were investigated as novel small molecule chaperone amplifiers. Lead optimization led to the discovery of compounds that displayed potent HSF1 activation activity, significant cytoprotection in MG-132 stress, ER stress and PolyQ stress cell models (EC50 < 10 mu M). (C) 2009 Published by Elsevier Ltd.