6,7-dichlorothiochroman-4-one | 66892-36-2

• 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: 6,7-dichlorothiochroman-4-one
• 英文别名: 6,7-dichloro-2,3-dihydrothiochromen-4-one
• CAS: 66892-36-2
• 化学式: C₉H₆Cl₂OS
• 分子量: 233.118
• InChiKey: DEPFMUTWHJRWNT-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C
• 沸点：
  389.1±42.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 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：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,7-dichlorothiochroman-4-one 在 溴 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 39.0h， 生成 7,8-dichloro-2-hydrazineyl-4H-thiochromeno[4,3-d]thiazole
  参考文献：
  名称：

  Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction

  摘要：

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.

  DOI：

  10.1021/jm401733v
• 作为产物：
  描述：

  3,4-二氯苯硫酚 在 硫酸 、 sodium hydroxide 作用下， 生成 6,7-dichlorothiochroman-4-one
  参考文献：
  名称：

  新型抗癌药α，β-环氧酮的设计与合成

  摘要：

  由于环氧官能团具有较高的抗癌活性，因此设计并合成了α，β-环氧酮作为新型抗癌剂，并通过UV，1 H NMR，IR，MS技术和元素分析确定了它们的结构。用MTT法评估了它们的体外抗癌活性，结果表明化合物4c对A-549，Hela和HepG2细胞的IC 50表现出良好的活性，IC 50分别为17.8、22.0和24.1 µg / mL。通过胃内给药的小鼠的LD50剂量为1864.4mg / kg。因此，α，β-环氧酮可能会提供新的抗癌药。

  DOI：

  10.1002/cjoc.201190153

文献信息

• Spiro Hydantoin Aldose Reductase Inhibitors
  作者：Reinhard Sarges、Rodney C. Schnur、John L. Belletire、Michael J. Peterson

  DOI：10.1021/jm00396a037

  日期：1988.1

  formation from glucose, catalyzed by the enzyme aldose reductase, is believed to play a role in the development of certain chronic complications of diabetes mellitus. Spiro hydantoins derived from five- and six-membered ketones fused to an aromatic ring or ring system inhibit aldose reductase isolated from calf lens. In vivo these compounds are potent inhibitors of sorbitol formation in sciatic nerves of

  据信由醛糖还原酶催化的葡萄糖形成山梨醇在糖尿病的某些慢性并发症的发生中起作用。源自与芳香族环或环系统融合的五元和六元酮的螺乙内酰脲抑制从小牛晶状体分离的醛糖还原酶。在体内，这些化合物是链脲佐剂化大鼠坐骨神经中山梨醇形成的有效抑制剂。在衍生自6-卤代的2,3-二氢-4H-1-苯并吡喃-4-酮（4-苯并二氢吡喃酮）的螺旋乙内酰脲中可达到最佳的体内活性。在2,4-二氢-6-氟螺[4H-1-苯并吡喃-4,4'-咪唑烷] -2'，5'-二酮中，活性仅存在于4S异构体化合物115（CP-45,634，USAN ：山梨醇）。该化合物目前正用于测试人体，
• Synthesis and biological evaluation of novel pyrazoline derivatives containing indole skeleton as anti-cancer agents targeting topoisomerase II
  作者：Yali Song、Siran Feng、Jiajia Feng、Jinjiao Dong、Kan Yang、Zhenming Liu、Xiaoqiang Qiao

  DOI：10.1016/j.ejmech.2020.112459

  日期：2020.8

  In order to develop potent anticaner agents, a novel series of 3-(1H-indol-3-yl)-2,3,3a,4-tetrahydrothiochromeno[4,3-c]pyrazole derivatives were synthesized. Structures of all compounds were confirmed. MTT assay has been employed to study antiproliferative activity of these compounds with four human cancer cell lines (MGC-803, Hela, MCF-7 and Bel-7404) and a normal cell line L929. Most of these compounds

  为了开发有效的抗癌剂，合成了一系列新的3-（1 H-吲哚-3-基）-2,3,3a，4-四氢硫代色素[4,3-c]吡唑衍生物。确认所有化合物的结构。MTT分析已用于研究这些化合物对四种人类癌细胞系（MGC-803，Hela，MCF-7和Bel-7404）和正常细胞系L929的抗增殖活性。这些化合物大多数在体外对正常细胞表现出潜在的抗癌活性和低细胞毒性。7d和7f显示出最佳的抗癌活性，其IC 50MGC-803的最大值分别为15.43μM和20.54μM。他们大多数表现出拓扑异构酶II选择性抑制。裂解反应分析和DNA解链分析表明7f为非嵌入的Topo II催化抑制剂，与对接结果一致。激光扫描共聚焦显微镜系统跟踪可以大量进入细胞核的代表性化合物7d和7f的位置。特别地，最有效的化合物7d和7f显示出能够诱导MGC-803细胞中的G2 / M细胞周期停滞和凋亡。
• Spiro-imidazolones for alleviating diabetes-associated conditions, processes for preparing them, and pharmaceutical compositions containing them
  申请人：PFIZER INC.

  公开号：EP0028485A1

  公开（公告）日：1981-05-13

  Spiro-imidazolones, useful for alleviating diabetes-associated conditions such as diabetic cataracts, retinopathy and neuropathy, of the formula:-H N and the pharmaceutically acceptable acid addition salts thereof, wherein W is -(CH2)n-; X is hydrogen and X is hydrogen, fluorine, chlorine, bromine, C1-C4 alkyl or C1-C4 alkoxy; or X and X1, when taken separately, are each chlorine, C1-C4 alkyl or C1-C4 alkoxy, and when taken together are -OCH2(CH2)nO-; Y is W, oxygen, sulfur, oxosulfur or dioxosulfur; and each n is independently zero or one; pharmaceutical compositions containing them, and processes for their preparation.

  用于缓解糖尿病相关病症（如糖尿病性白内障、视网膜病变和神经病变）的螺咪唑啉酮，其式为：-H N 及其药学上可接受的酸加成盐，其中 W 是-(CH2)n-； X 是氢，X 是氢、氟、氯、溴、C1-C4 烷基或 C1-C4 烷氧基；或 X 和 X1 分别为氯、C1-C4 烷基或 C1-C4 烷氧基，合在一起为-OCH2(CH2)nO-； Y 是 W、氧、硫、氧硫或二氧硫；每个 n 独立地为 0 或 1；含有它们的药物组合物及其制备工艺。
• SARGES, R.
  作者：SARGES, R.

  DOI：——

  日期：——
• SARGES, REINHARD;SCHNUR, RODNEY C.;BELLETIRE, JOHN L.;PETERSON, MICHAEL J+, J. MED. CHEM., 31,(1988) N 1, 230-243
  作者：SARGES, REINHARD、SCHNUR, RODNEY C.、BELLETIRE, JOHN L.、PETERSON, MICHAEL J+

  DOI：——

  日期：——