间(二氟甲硫基)苯甲酰氯 | 261944-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 间(二氟甲硫基)苯甲酰氯
• 中文别名: 3-(二氟甲基硫代)苯甲酰氯
• 英文名称: 3-(Difluoromethylthio)Benzoyl Chloride
• 英文别名: 3-(difluoromethylsulfanyl)benzoyl chloride
• CAS: 261944-16-5
• 化学式: C₈H₅ClF₂OS
• mdl: MFCD01631523
• 分子量: 222.643
• InChiKey: RLWSFTJAJPGBMY-UHFFFAOYSA-N

物化性质

• 沸点：
  85-88°C 8mm
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R34
• 海关编码：
  2930909090
• 危险品运输编号：
  UN 3265

反应信息

• 作为反应物：
  描述：

  间(二氟甲硫基)苯甲酰氯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.5h， 生成 D-81196
  参考文献：
  名称：

  Synthetic 2-Aroylindole Derivatives as a New Class of Potent Tubulin-Inhibitory, Antimitotic Agents

  摘要：

  A new class of simple synthetic antimitotic compounds based on 2-aroylindoles was discovered. (5-Methoxy-1H-2-indolyl)-phenylmethanone (1) as well as analogous 3-fluorophenyl- (36) and 3-methoxyphenyl (3) derivatives displayed high cytotoxicity Of IC50 = 20 to 75 nM against the human HeLa/KB cervical, SK-OV-3 ovarian, and U373 astrocytoma carcinoma cell lines. The inhibition of proliferation correlated with the arrest in the G2/M phase of the cell cycle. In in vitro assays with tubulin isolated from bovine brain, in general antiproliferative activity correlated with inhibition of tubulin polymerization. Thus, the antimitotic activity of 2-aroylindoles is explained by interference with the mitotic spindle apparatus and destabilization of microtubules. In contrast to colchicine, vincristine, nocodazole, or taxol, I did not significantly affect the GTPase activity of beta -tubulin. Interestingly, selected compounds inhibited angiogenesis in the chorioallantoic membrane (CAM) assay. In xenograft experiments, 1 was highly active after oral administration at 200 mg/kg against the human amelanocytic melanoma MEXF 989 in athymic nude mice. We conclude, that 2-aroylindoles constitute an interesting new class of antitubulin agents with the potential to be clinically developed for cancer treatment.

  DOI：

  10.1021/jm010940+
• 作为产物：
  描述：

  间(二氟甲硫基)苯甲酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 间(二氟甲硫基)苯甲酰氯
  参考文献：
  名称：

  EP1544202

  摘要：

  公开号：

文献信息

• Discovery of Imidazo[1,2-<i>b</i>]thiazole Derivatives as Novel SIRT1 Activators
  作者：Chi B. Vu、Jean E. Bemis、Jeremy S. Disch、Pui Yee Ng、Joseph J. Nunes、Jill C. Milne、David P. Carney、Amy V. Lynch、Jesse J. Smith、Siva Lavu、Philip D. Lambert、David J. Gagne、Michael R. Jirousek、Simon Schenk、Jerrold M. Olefsky、Robert B. Perni

  DOI：10.1021/jm8012954

  日期：2009.3.12

  series of imidazo[1,2-b]thiazole derivatives is shown to activate the NAD+-dependent deacetylase SIRT1, a potential new therapeutic target to treat various metabolic disorders. This series of compounds was derived from a high throughput screening hit bearing an oxazolopyridine core. Water-solubilizing groups could be installed conveniently at either the C-2 or C-3 position of the imidazo[1,2-b]thiazole

  已显示一系列咪唑并[1,2- b ]噻唑衍生物可激活NAD +依赖性脱乙酰基酶SIRT1，这是治疗各种代谢疾病的潜在新治疗靶标。该系列化合物是从带有恶唑烷吡啶核的高通量筛选命中获得的。水溶性基团可方便地安装在咪唑并[1,2- b ]噻唑环的C-2或C-3位置。可以通过修饰这些咪唑并[1,2- b ]噻唑衍生物的酰胺部分来调节SIRT1酶的活性。该系列中最有效的类似物，即化合物29，已在ob / ob小鼠模型，饮食诱发的肥胖（DIO）小鼠模型和Zucker fa / fa大鼠模型中证明了口服降糖活性。
• Solid phase combinatorial synthesis of benzothiazoles and evaluation of topoisomerase II inhibitory activity
  作者：Suk-June Choi、Hyen Joo Park、Sang Kook Lee、Sang Woong Kim、Gyoonhee Han、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2005.09.051

  日期：2006.2

  To investigate one possible mechanism of action of the cytotoxic activity of benzothiazoles, we synthesized 2-(substituted-phenyl)benzothiazoles and evaluated their ability to inhibit topoisomerase 11 activities. Solid phase combinatorial method using trityl resin was employed and benzothiazole derivatives with Various substitution on 2'-, 3'-, or 4'-position of phenyl group were obtained in ca. 30 mg scale (7-96% yield). Most of the compounds synthesized exhibited topoisomerase 11 inhibitory activity at 100 mu M. 2-(3-Amino-4-methylphenyl)benzothiazole showed high activity (IC50 = 71.7 mu M), comparable to etoposide (IC50 = 78.4 mu M). (c) 2005 Elsevier Ltd. All rights reserved.