2-(4-氯苯基)-6-吗啉-4-硫代吡喃-4-酮 | 500169-20-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(4-氯苯基)-6-吗啉-4-硫代吡喃-4-酮
• 中文别名: 2-(2-呋喃)-1,3-噻唑-4-碳酰氯
• 英文名称: 2-(4-chlorophenyl)-6-morpholino-4H-thiopyran-4-one
• 英文别名: 2-(4-Chlorophenyl)-6-morpholin-4-yl-thiopyran-4-one；2-(4-chlorophenyl)-6-morpholin-4-ylthiopyran-4-one
• CAS: 500169-20-0
• 化学式: C₁₅H₁₄ClNO₂S
• 分子量: 307.801
• InChiKey: WVAMXZOUPLIOOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(4-氯苯基)-6-吗啉-4-硫代吡喃-4-酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 various solvent(s) 为溶剂， 反应 18.0h， 以67%的产率得到3-Bromo-6-(4-chlorophenyl)-2-morpholin-4-yl-thiopyran-4-
  参考文献：
  名称：

  Pyranone, Thiopyranone, and Pyridone Inhibitors of Phosphatidylinositol 3-Kinase Related Kinases. Structure−Activity Relationships for DNA-Dependent Protein Kinase Inhibition, and Identification of the First Potent and Selective Inhibitor of the Ataxia Telangiectasia Mutated Kinase

  摘要：

  Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholino-pyran-4-ones and 2-morpholino-thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6-(morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.

  DOI：

  10.1021/jm061121y
• 作为产物：
  描述：

  6-(4-chlorophenyl)-2-mercapto-4H-thiopyran-4-one 在 potassium carbonate 作用下， 以 乙二醇 、 丙酮 为溶剂， 生成 2-(4-氯苯基)-6-吗啉-4-硫代吡喃-4-酮
  参考文献：
  名称：

  2,6-Disubstituted pyran-4-one and thiopyran-4-one inhibitors of DNA-Dependent protein kinase (DNA-PK)

  摘要：

  6-Aryl-2-morpholin-4-yl-4H-pyran-4-ones and 6-aryl-2-morpholin-4-yl-4H-thiopyran-4-ones were synthesised and evaluated as potential inhibitors of the DNA repair enzyme DNA-dependent protein kinase (DNA-PK). Several compounds in each series exhibited superior activity to the chromenone LY294002, and were of comparable potency to the benzochromenone NU7026 (IC50=0.23 muM). Importantly, members of both structural classes were found to be selective inhibitors of DNA-PK over related phosphatidylinositol 3-kinase-related kinase (PIKK) family members. A multiple-parallel synthesis approach, employing Suzuki cross-coupling methodology, was utilised to prepare libraries of thiopyran-4-ones with a range of aromatic groups at the 3'- and 4'-positions on the thiopyran-4-one 6-aryl ring. Screening of the libraries resulted in the identification of 6-aryl-2-morpholin-4-yl-4H-thiopyran-4-ones bearing naphthyl or benzo[b]thienyl substituents at the 4'-position, as potent DNA-PK inhibitors with IC50 values in the 0.2-0.4 muM range. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00652-8

文献信息

• Process for preparation of cyclohexanone oxime
  申请人：——

  公开号：US20040176592A1

  公开（公告）日：2004-09-09

  A method for producing cyclohexanone oxime, which comprises the steps of (1) subjecting to an amination reaction a starting material selected from the group consisting of cyclohexanol, cyclohexanone and a mixture thereof, thereby obtaining cyclohexylamine, and (2) subjecting the obtained cyclohexylamine to a partial oxidation reaction, thereby obtaining cyclohexanone oxime, wherein a by-product (&agr;) formed in the step (1) and/or a by-product (&bgr;) formed in the step (2) are/is recycled to a reaction system of the amination reaction in the step (1).

  一种生产环己酮肟的方法，包括以下步骤：（1）对选自环己醇、环己酮和二者混合物的起始材料进行氨化反应，从而得到环己基胺；（2）将得到的环己基胺进行部分氧化反应，从而得到环己酮肟，其中在步骤（1）中形成的副产物（α）和/或在步骤（2）中形成的副产物（β）被循环利用到步骤（1）中的氨化反应的反应系统中。
• Process for producing lactam
  申请人：——

  公开号：US20040215013A1

  公开（公告）日：2004-10-28

  A method for producing a lactam, which comprises subjecting an alicyclic primary amine to an oxidation reaction in the presence of a catalyst comprising a silicon oxide, to thereby obtain a lactam. A catalyst comprising a silicon oxide which is for use in the above-mentioned method.

  一种生产内酰胺的方法，包括将脂环原始胺置于存在硅氧化物催化剂的氧化反应中，从而获得内酰胺。一种包括硅氧化物的催化剂，用于上述方法。
• Thiopyrane-4-ones as dna protein kinase inhibitors
  申请人：Martin Morrison Barr Niall

  公开号：US20050107367A1

  公开（公告）日：2005-05-19

  The present invention provides compounds of formula (I) and isomers, salts, solvates, chemically protected forms, and prodrugs thereof, wherein R 1 and R 2 are independently hydrogen, an option ally 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; and R 3 is an optionally substituted C 3-20 heterocyclyl or C 5-20 aryl group, and their use as pharmaceuticals, particularly in treating diseases which are retroviral mediated or ameliorated by the inhibition of DNA-PK,

  本发明提供了式（I）的化合物及其异构体、盐、溶剂合物、化学保护形式和前药，其中R1和R2独立地为氢、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一个具有4至8个环原子的可选取代的杂环环；R3为可选取代的C3-20杂环基或C5-20芳基，以及它们在药物学中的应用，特别是在治疗由逆转录病毒介导或通过抑制DNA-PK改善的疾病中。
• Method for preparing aromatic secondary amino compound
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0588060A2

  公开（公告）日：1994-03-23

  [Constitution] A method for preparing diphenylamine from cyclohexanone and aniline by adding dropwise nitrobenzene and cyclohexanone to a reaction system in which a hydrogen transfer catalyst and a sulfur-free polar solvent are present and aniline is being formed from nitrobenzene as a hydrogen acceptor. [Effect] Diphenylamine can be obtained in a high yield under moderate reaction conditions.

  [制法]一种从环己酮和苯胺制备二苯胺的方法，方法是将硝基苯和环己酮滴加到存在氢转移催化剂和无硫极性溶剂的反应体系中，苯胺作为氢接受体从硝基苯中生成。 [效果]在中等反应条件下，可以高产率获得二苯胺。
• [5C + 1S] Annulation:  A Facile and Efficient Synthetic Route toward Functionalized 2,3-Dihydrothiopyran-4-ones
  作者：Xihe Bi、Dewen Dong、Yan Li、Qun Liu、Qian Zhang

  DOI：10.1021/jo052032g

  日期：2005.12.1

  A facile and efficient synthetic route toward highly substituted 2,3-dihydrothiopyran-4-ones 2 has been developed via a formal [5C + 1S] annulation of readily available alpha-alkenoyl ketene-(S,S)-acetals 1 with sodium sulfide nonahydrated salt (Na(2)S(.)9H(2)O) and utilized in the synthesis of 2-(4-chlorophenyl)-6-(morpholin-4-yl)-4H-thiopyran-4-one 51, an inhibitor of DNA-dependent protein kinase (DNA-PK).