p-tolylsulfanyl-acetaldehyde dimethylacetal | 57860-45-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: p-tolylsulfanyl-acetaldehyde dimethylacetal
• 英文别名: p-Tolylmercapto-acetaldehyd-dimethylacetal；4-methyl-1-(2,2-dimethoxy-ethyl-sulfanyl)-benzene；(2,2-Dimethoxyethyl)(p-tolyl)sulfane；1-(2,2-dimethoxyethylsulfanyl)-4-methylbenzene
• CAS: 57860-45-4
• 化学式: C₁₁H₁₆O₂S
• 分子量: 212.313
• InChiKey: IWCUZRSJEBDZSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  170-175 °C(Press: 15 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-tolylsulfanyl-acetaldehyde dimethylacetal 在 磷酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 5-甲基苯并噻吩
  参考文献：
  名称：

  Antitumor Agents. 284. New Desmosdumotin B Analogues with Bicyclic B-Ring as Cytotoxic and Antitubulin Agents

  摘要：

  We previously reported that the biological activity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI(50) values of 0.8-2.1 mu M. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) over-expressing multidrug resistant cell line. We have now prepared and evaluated, 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI(50) values of 0.06-0.16 mu M, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC(50) value of 2.0 mu M and colchicine binding by 7896 as well as cellular microtubule polymerization and spindle formation.

  DOI：

  10.1021/jm1011947
• 作为产物：
  描述：

  2-氯乙醛缩二甲醇 、 4-甲苯硫酚 在 sodium methylate 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 p-tolylsulfanyl-acetaldehyde dimethylacetal
  参考文献：
  名称：

  Antitumor Agents. 284. New Desmosdumotin B Analogues with Bicyclic B-Ring as Cytotoxic and Antitubulin Agents

  摘要：

  We previously reported that the biological activity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI(50) values of 0.8-2.1 mu M. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) over-expressing multidrug resistant cell line. We have now prepared and evaluated, 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI(50) values of 0.06-0.16 mu M, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC(50) value of 2.0 mu M and colchicine binding by 7896 as well as cellular microtubule polymerization and spindle formation.

  DOI：

  10.1021/jm1011947

文献信息

• Ple, Patrick A.; Marnett, Lawrence J., Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1271 - 1272
  作者：Ple, Patrick A.、Marnett, Lawrence J.

  DOI：——

  日期：——
• Sunthankar; Tilak, Proceedings - Indian Academy of Sciences, Section A, 1950, # 32, p. 396,401
  作者：Sunthankar、Tilak

  DOI：——

  日期：——
• PLE, PATRICK A.;MARNETT, LAWRENCE J., J. HETEROCYCL. CHEM., 25,(1988) N 4, C. 1271-1272
  作者：PLE, PATRICK A.、MARNETT, LAWRENCE J.

  DOI：——

  日期：——
• SUBSTITUTED SULFONIC ACID N- (AMINOIMINOMETHYL)PHENYLALKYL]-AZAHETEROCYCLAMIDE COMPOUNDS
  申请人：RHONE-POULENC RORER PHARMACEUTICALS, INC.

  公开号：EP0894088A1

  公开（公告）日：1999-02-03
• EP0894088A4
  申请人：——

  公开号：EP0894088A4

  公开（公告）日：2001-12-05