3-bromo-4H-thiochromen-4-one | 68847-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 3-bromo-4H-thiochromen-4-one
• 英文别名: 3-bromothiochromen-4-one；3-Bromo-thiochromone；3-bromothiochromone；3-bromo-thiochromen-4-one；3-Brom-thiochromen-4-on；3-Bromthiochromen-4-on
• CAS: 68847-94-9
• 化学式: C₉H₅BrOS
• mdl: MFCD03426761
• 分子量: 241.108
• InChiKey: HNGUKFYOSVSQJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-4H-thiochromen-4-one 在 sodium azide 作用下， 以 甲醇 、 水 为溶剂， 反应 11.0h， 生成 Diethyl <<(4-Oxo-4H<1>benzothiopyran-3-yl)amino>methylene>propanedioate
  参考文献：
  名称：

  4,10-二氢-4,10-二氧代-1 H [1]苯并硫代吡喃并[3,2- B ]吡啶和7-氧代7,13-二氢[1]苯并硫代吡喃并[2,3- b ]-的合成1,5-苯二氮卓

  摘要：

  通过使3-溴-硫代色素-4-酮与叠氮化钠在甲醇-水中反应，可轻松制得3-氨基-4 H -1-苯并噻喃-4-酮（3-氨基噻吩酮）。3-氨基硫代色酮与乙氧基亚甲基丙二酸二乙酯和乙酰二羧酸二甲酯缩合，得到中间体，将其热环化得到4,10-二氢-4,10-dioxo-1 H [1]苯并硫代吡喃并[3,2- b ]吡啶羧酸酯。将3-甲酰基-硫代色酮与邻苯二胺缩合，得到7-氧代-7,13-二氢[1]苯并硫代吡喃并[2,3 - b ] -1,5-苯并二氮杂。

  DOI：

  10.1002/jhet.5570220123
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 作用下， 生成 3-bromo-4H-thiochromen-4-one
  参考文献：
  名称：

  Arndt, Chemische Berichte, 1925, vol. 58, p. 1631

  摘要：

  DOI：

文献信息

• A Direct Organocatalytic Enantioselective Route to Functionalized <i>trans</i> ‐Diels–Alder Products Having the Norcarane Scaffold
  作者：Casper L. Barløse、Niklas L. Østergaard、René S. Bitsch、Marc V. Iversen、Karl Anker Jørgensen

  DOI：10.1002/anie.202106598

  日期：2021.8.9

  organocatalysis with excellent selectivity, high yield and up to five contiguous stereocenters is presented. The reaction concept integrates the halogen effect and a novel discovered pseudo-halogen effect to direct an endo-selective, secondary-amine catalyzed Diels–Alder reaction allowing for the subsequent formation of trans-Diels–Alder cycloadducts featuring the norcarene scaffold. The methodology relies on

  提出了一种通过有机催化构建 trans-Diels-Alder 支架的对映选择性方法，具有优异的选择性、高产率和多达五个连续的立体中心。该反应概念整合了卤素效应和新发现的拟卤素效应，以指导内选择性、仲胺催化的 Diels-Alder 反应，从而允许随后形成具有降蒎烯骨架的反式 Diels-Alder 环加合物。该方法依赖于原位生成的三烯胺与 α-溴化或 α-伪卤化烯酮之间的反应，以形成短暂的顺式 Diels-Alder 中间体。由（伪）卤素效应增强的内过渡态设置了立体化学，允许随后的 S N在三级中心进行类似 2 的反应以获得 trans-Diels-Alder 支架。该机制得到了实验结果和计算研究的研究和支持。
• Chromone derivative, process for preparing same and pharmaceutical composition
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP0758649A1

  公开（公告）日：1997-02-19

  A chromone derivative of the formula (I): wherein R11 is a pyrazolyl, pyrrolyl, triazolyl, benzotriazolyl, benzimidazolyl, indazolyl, or indolyl group, R2, R3, R4, and R5 is independently a hydrogen or halogen atom, or a hydroxy or alkoxy group, or an alkoxy group substituted with one or more alkoxy groups, and X is an oxygen or sulfur atom, or a salt thereof is disclosed. The chromone derivative inhibits the activity of matrix metalloproteinase.

  一种式(I)的铬酮衍生物： 其中 R11 是吡唑基、吡咯基、三唑基、苯并三唑基、苯并咪唑基、吲唑基或吲哚基，R2、R3、R4 和 R5 独立地是氢原子或卤素原子，或羟基或烷氧基，或被一个或多个烷氧基取代的烷氧基，X 是氧原子或硫原子，或其盐。铬酮衍生物可抑制基质金属蛋白酶的活性。
• Discovery of Potent, Orally Bioavailable Phthalazinone Bradykinin B1 Receptor Antagonists
  作者：Kaustav Biswas、Tanya A. N. Peterkin、Marian C. Bryan、Leyla Arik、Sonya G. Lehto、Hong Sun、Feng-Yin Hsieh、Cen Xu、Robert T. Fremeau、Jennifer R. Allen

  DOI：10.1021/jm200808v

  日期：2011.10.27

  The bradykinin B1 receptor is rapidly induced upon tissue injury and inflammation, stimulating the production of inflammatory mediators resulting in plasma extravasation, leukocyte trafficking, edema, and pain. We have previously reported on sulfonamide and sulfone-based B1 antagonists containing a privileged bicyclic amine moiety leading to potent series of 2-oxopiperazines. The suboptimal pharmacokinetics and physicochemical properties of the oxopiperazine sulfonamides led us to seek B1 antagonists with improved druglike properties. Using a pharmacophore model containing a bicyclic amine as anchor, we designed a series of amide antagonists with targeted physicochemical properties. This approach led to a novel series of potent phthalazinone B1 antagonists, where we successfully replaced a sulfonamide acceptor with a cyclic carbonyl unit. SAR studies revealed compounds with subnanomolar B1 binding affinity. These compounds demonstrate excellent cross-species PK properties with high oral bioavailability and potent activity in a rabbit biochemical challenge pharmacodynamic study.
• Still, Ian W.J.; Leong, Toong S., Canadian Journal of Chemistry, 1980, vol. 58, p. 369 - 375
  作者：Still, Ian W.J.、Leong, Toong S.

  DOI：——

  日期：——
• Nambara, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 624,626
  作者：Nambara

  DOI：——

  日期：——