6,8-dibromo-1,1-dioxo-1-thiochroman-4-one | 909248-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 6,8-dibromo-1,1-dioxo-1-thiochroman-4-one
• 英文别名: 6,8-Dibromo-1,1-dioxo-2,3-dihydrothiochromen-4-one
• CAS: 909248-36-8
• 化学式: C₉H₆Br₂O₃S
• 分子量: 354.019
• InChiKey: RCYALVWOGXQGLP-UHFFFAOYSA-N

物化性质

• 沸点：
  531.3±50.0 °C(Predicted)
• 密度：
  2.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-dibromo-1,1-dioxo-1-thiochroman-4-one 、 氨基硫脲 在 甲醇 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.25h， 以44%的产率得到6,8-dibromo-1,1-dioxo-1-thiochroman-4-one thiosemicarbazone
  参考文献：
  名称：

  INHIBITORS OF CYSTEINE PROTEASES AND METHODS OF USE THEREOF

  摘要：

  本发明涉及半胱氨酸蛋白酶的半胱氨酸脒或硫代半胱氨酸脒抑制剂，以及使用这类化合物预防和治疗原虫感染，如锥虫病、疟疾和利什曼病的方法。这些化合物还可用于抑制与癌变有关的半胱氨酸蛋白酶，包括半胱氨酸蛋白酶B和L。

  公开号：

  US20090076076A1
• 作为产物：
  描述：

  硫代色满-4-酮 在 三氯化铝 、 双氧水 、 溴 、 溶剂黄146 作用下， 反应 1.0h， 生成 6,8-dibromo-1,1-dioxo-1-thiochroman-4-one
  参考文献：
  名称：

  Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas’ disease

  摘要：

  A series of compounds bearing tetrahydronaphthalene, benzophenone, propiophenone, and related rigid molecular skeletons functionalized with thiosemicarbazone or unsaturated carbonyl moieties were prepared by chemical synthesis and evaluated for their ability to inhibit the enzyme cruzain. As potential treatment agents for Chagas' disease, three compounds from the group demonstrate potent inhibition of cruzain with IC50 values of 17, 24, and 80 nM, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.041

文献信息

• US8173696B2
  申请人：——

  公开号：US8173696B2

  公开（公告）日：2012-05-08
• INHIBITORS OF CYSTEINE PROTEASES AND METHODS OF USE THEREOF
  申请人：Siles Rogelio

  公开号：US20090076076A1

  公开（公告）日：2009-03-19

  The present invention relates to semicarbazone or thiosemicarbazone inhibitors of cysteine proteases and methods of using such compounds to prevent and treat protozoan infections such as trypanosomiasis, malaria and leishmaniasis. The compounds also find use in inhibiting cysteine proteases associated with carcinogenesis, including cathepsins B and L.

  本发明涉及半胱氨酸蛋白酶的半胱氨酸脒或硫代半胱氨酸脒抑制剂，以及使用这类化合物预防和治疗原虫感染，如锥虫病、疟疾和利什曼病的方法。这些化合物还可用于抑制与癌变有关的半胱氨酸蛋白酶，包括半胱氨酸蛋白酶B和L。
• Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas’ disease
  作者：Rogelio Siles、Shen-En Chen、Ming Zhou、Kevin G. Pinney、Mary Lynn Trawick

  DOI：10.1016/j.bmcl.2006.05.041

  日期：2006.8

  A series of compounds bearing tetrahydronaphthalene, benzophenone, propiophenone, and related rigid molecular skeletons functionalized with thiosemicarbazone or unsaturated carbonyl moieties were prepared by chemical synthesis and evaluated for their ability to inhibit the enzyme cruzain. As potential treatment agents for Chagas' disease, three compounds from the group demonstrate potent inhibition of cruzain with IC50 values of 17, 24, and 80 nM, respectively. (c) 2006 Elsevier Ltd. All rights reserved.