4-hydroxy-2-deoxy-2-thiocoumarin | 70685-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-hydroxy-2-deoxy-2-thiocoumarin
• 英文别名: 4-hydroxy-2H-chromen-2-thione；4-hydroxy-2-thiocoumarin；4-hydroxythionecoumarin；4-hydroxythiocoumarin
• CAS: 70685-46-0
• 化学式: C₉H₆O₂S
• 分子量: 178.211
• InChiKey: UYTWKZKDNIKGAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-deoxy-2-thiocoumarin 在 叔丁基过氧化氢 、 碘 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 2-((1H-indol-3-yl)sulfonyl)-4H-chromen-4-one
  参考文献：
  名称：

  氧化交叉脱氢偶联反应从4-羟基-2H-色烯-2-硫酮和吲哚合成3-硫基吲哚衍生物及其部分砜衍生物的抗增殖活性研究

  摘要：

  通过采用氧化交叉脱氢偶联反应，由 4-羟基硫代香豆素和吲哚合成了一类新型的 3-硫基吲哚衍生物。对六种砜类衍生物进行了靶点预测和对接研究，并选择了四种砜类衍生物进行进一步的体外研究。图 1. 3-磺基吲哚和一些砜衍生物的合成。

  DOI：

  10.1016/j.bioorg.2023.106900
• 作为产物：
  描述：

  4-羟基香豆素 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以85%的产率得到4-hydroxy-2-deoxy-2-thiocoumarin
  参考文献：
  名称：

  Fahmy, A. A.; Hafez, T. S.; El-Farargy, A. F., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 57, # 3/4, p. 211 - 215

  摘要：

  DOI：

文献信息

• Cyclization reactions of coumarin derivatives: Chemo- and regioselectivity effects of oxygen/sulfur isosteric replacement
  作者：Giovanni Palmisano、Lucio Toma、Rita Annunziata、Silvia Tagliapietra、Alessandro Barge、Giancarlo Cravotto

  DOI：10.1002/jhet.5570440221

  日期：2007.3

  We synthesized several sulfur isosters of ferulenol and related prenylcoumarins from Ferula communis preliminary to finding whether the antitubercular activity of these natural compounds might be dissociated from their antithrombin activity. Direct thionation of ferprenine, an instance of “diversity-oriented” synthesis, yielded a mixture of three thiocoumarin derivatives. When 4-hydroxy-2-deoxy-2-thiocoumarin

  我们从Ferula communis合成了几种阿魏烯醇和相关异戊二烯香豆素的硫等排体初步发现这些天然化合物的抗结核活性是否可能与其抗凝血酶活性分离。所谓的“以多样性为导向”合成的实例是直接对硫丁胺进行硫磺化，生成了三种硫代香豆素衍生物的混合物。当4-羟基-2-脱氧-2-硫代香豆素与法呢醛和其他α，β-不饱和醛反应时，位置2的等位氧-硫取代令人惊讶地引起串联Knoevenagel-电环反应中的区域化学转化，普遍提供线性加合物。广泛调查了各种替代的食用油，突显出Knoevenagel和Michael加成之间的竞争。通过考虑空间和电子因素以及与催化剂形成复合物的能量计算，使该结果合理化。
• RODENTICIDAL COMPOUND, COMPOSITION INCLUDING SAME AND USE FOR COMBATING RODENT PESTS
  申请人：Caruel Herve

  公开号：US20140187625A1

  公开（公告）日：2014-07-03

  A novel compound obtained from molecules of the coumarin family, which exhibits rodenticidal activity. Also, compositions which incorporate such compounds and the use thereof for combating rodent pests.

  一种从香豆素家族分子中获得的新化合物，具有杀鼠活性。此外，还包括含有这种化合物的组合物及其用于对抗啮齿类害虫的用途。
• Formal [3+3] cycloaddition reaction of 4-hydroxythiocoumarin to 4Н-chromene-3-carbaldehydes: synthesis of thiochromeno[3',4':5,6]pyrano[2,3-b]chromen-6-ones
  作者：Irina A. Semenova、Dmitry V. Osipov、Yulia V. Popova、Vitaly A. Osyanin、Oleg P. Demidov、Yuri N. Klimochkin

  DOI：10.1007/s10593-020-02801-6

  日期：2020.9

  A cascade reaction of 4-hydroxythiocoumarin and 4Н-chromene-3-carbaldehydes was developed, consisting of Knoevenagel condensation and oxa-6π electrocyclization in the presence of ammonium acetate as catalyst. A series of polycyclic acetals containing a fused thiocoumarin moiety were obtained.

  4- hydroxythiocoumarin和4所述的级联反应Н色烯-3- carbaldehydes被开发，在乙酸铵的存在下作为催化剂由Knoevenagel缩合和氧杂- 6πelectrocyclization的。获得一系列含有稠合的硫香豆素部分的多环缩醛。
• [EN] DNA-PK INHIBITORS<br/>[FR] INHIBITEURS D'ADN-PK
  申请人：CANCER REC TECH LTD

  公开号：WO2003024949A1

  公开（公告）日：2003-03-27

  The invention relates to the use of compounds of formula (I) and isomers, salts, solvates, chemically protected forms, and prodrugs thereof, in the preparation of a medicament for inhibiting the activity of DNA-PK, wherein R?1 and R2¿ are independently hydrogen, an optionally substituted C¿1-7? alkyl group, C3-20 heterocyclyl group, or C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; X and Y are selected from CR?4¿ and O, O and CR'4 and NR'4 and N, where the unsaturation is in the appropriate place in the ring, and where one of R?3 and R4 or R'4¿ is an optionally substituted C¿3-20? heteroaryl or C5-20 aryl group, and the other of R?3 and R4 or R'4¿ is H, or R?3 and R4 or R'4¿ together are -A-B-, which collectively represent a fused optionally substituted aromatic ring. The compounds also selectively inhibit the activity of DNA-PK compared to PI 3-kinase and/or ATM.

  本发明涉及使用式(I)化合物及其异构体、盐、溶剂合物、化学保护形式和前药，在制备用于抑制DNA-PK活性的药物中使用，其中R?1和R2¿分别为氢、可选取代的C¿1-7?烷基、C3-20杂环基或C5-20芳基，或者可以与它们连接的氮原子一起形成具有4到8个环原子的可选取代杂环环；X和Y从CR?4¿和O、O和CR'4和NR'4和N中选取，其中不饱和度在环中适当位置，其中R?3和R4或R'4¿中的一个为可选取代的C¿3-20?杂芳基或C5-20芳基，而另一个为H，或者R?3和R4或R'4¿一起是-A-B-，它们共同代表一个融合的可选取代芳香环。这些化合物还比PI 3-激酶和/或ATM选择性地抑制DNA-PK活性。
• Dna-pk inhibitors
  申请人：——

  公开号：US20040192687A1

  公开（公告）日：2004-09-30

  The invention relates to the use of compounds of formula (I) and isomers, salts, solvates, chemically protected forms, and prodrugs thereof, in the preparation of a medicament for inhibiting the activity of DNA-PK, wherein R 1 and R 2 are independently hydrogen, an optionally substituted C 1-7 alkyl group, C 3-20 heterocyclyl group, or C 5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; X and Y are selected from CR 4 and O, O and CR′ 4 and NR″ 4 and N, where the unsaturation is in the appropriate place in the ring, and where one of R 3 and R 4 or R′ 4 is an optionally substituted C 3-20 heteroaryl or C 5-20 aryl group, and the other of R 3 and R 4 or R′ 4 is H, or R 3 and R 4 or R″ 4 together are —A—B—, which collectively represent a fused optionally substituted aromatic ring. The compounds also selectively inhibit the activity of DNA-PK compared to PI 3-kinase and/or ATM. 1

  本发明涉及使用式(I)化合物及其异构体、盐、溶剂合物、化学保护形式及其前药，在制备抑制DNA-PK活性的药物方面使用。其中，R1和R2分别为氢、可选取代的C1-7烷基、C3-20杂环基或C5-20芳基，或者与它们连接的氮原子一起形成含有4到8个环原子的可选取代杂环环；X和Y从CR4和O、O和CR'4以及NR"4和N中选择，其中不饱和度在环中适当位置，且R3和R4或R'4中的一个为可选取代的C3-20杂芳基或C5-20芳基，而另一个为氢，或者R3和R4或R"4一起为-A-B-，它们共同表示一个融合的可选取代芳香环。这些化合物与PI 3-激酶和/或ATM相比，也具有选择性抑制DNA-PK活性的作用。