3,4,5-trimethoxyphenyl-(1-phenylsulfonyl-1H-2-indolyl)-methanone | 370580-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,4,5-trimethoxyphenyl-(1-phenylsulfonyl-1H-2-indolyl)-methanone
• 英文别名: 1-phenylsulfonyl-1H-2-indolyl(3,4,5-trimethoxyphenyl)-1-methanone；[1-(Benzenesulfonyl)indol-2-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 370580-26-0
• 化学式: C₂₄H₂₁NO₆S
• 分子量: 451.5
• InChiKey: BYPHOAXQPPSQLK-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  665.8±65.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxyphenyl-(1-phenylsulfonyl-1H-2-indolyl)-methanone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (1H-indol-2-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  4- and 5-Aroylindoles as Novel Classes of Potent Antitubulin Agents

  摘要：

  A novel series of 4- and 5-aroylindole derivatives was prepared and evaluated for antitumor activity. Several compounds showed excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 13, 14, 15, and 18, with IC50 values of 1.9, 1.1, 1.2, and 1.8 mu M, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine. They also displayed antiproliferative activity, with IC50 values ranging from 10 to 43 nM in a variety of human cell lines from different organs.

  DOI：

  10.1021/jm070557q
• 作为产物：
  描述：

  1-(苯磺酰)-1H-吲哚-2-甲醛 在 重铬酸吡啶 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3,4,5-trimethoxyphenyl-(1-phenylsulfonyl-1H-2-indolyl)-methanone
  参考文献：
  名称：

  4- and 5-Aroylindoles as Novel Classes of Potent Antitubulin Agents

  摘要：

  A novel series of 4- and 5-aroylindole derivatives was prepared and evaluated for antitumor activity. Several compounds showed excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 13, 14, 15, and 18, with IC50 values of 1.9, 1.1, 1.2, and 1.8 mu M, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine. They also displayed antiproliferative activity, with IC50 values ranging from 10 to 43 nM in a variety of human cell lines from different organs.

  DOI：

  10.1021/jm070557q

文献信息

• 2-acyl indole derivatives and their use as antitumor agents
  申请人：——

  公开号：US20020091124A1

  公开（公告）日：2002-07-11

  The invention relates to novel indole and heteroindole derivatives of the formula I 1 to their tautomers, their stereoisomers, their mixtures and their salts, to their preparation and to the use of indole derivatives of the formula I as antitumor agents.

  这项发明涉及到式I的新型吲哚和杂吲哚衍生物，以及它们的互变异构体、立体异构体、混合物和盐，以及它们的制备和将式I的吲哚衍生物用作抗肿瘤药剂。
• INDOLES, DERIVATIVES AND ANALOGS THEREOF AND USES THEREFOR
  申请人：DALTON James T.

  公开号：US20120022121A1

  公开（公告）日：2012-01-26

  Indole derivatives and analogous compounds and pharmaceutical compositions comprising the same are provided. Also provided are methods of using these compounds to inhibit tubulin polymerization in a cell associated with a proliferative disease or to treat cancer, metastatic cancer, resistant cancer or multidrug resistant cancer, including inter-alia: prostate cancer, breast cancer, melanoma, colon cancer and bladder cancer.

  本文提供吲哚衍生物及其类似化合物和含有这些化合物的制药组合物。还提供了使用这些化合物抑制与增殖性疾病相关的细胞中的微管聚合或治疗癌症、转移性癌症、耐药癌症或多药耐药癌症的方法，包括但不限于前列腺癌、乳腺癌、黑色素瘤、结肠癌和膀胱癌。
• Synthetic 2-Aroylindole Derivatives as a New Class of Potent Tubulin-Inhibitory, Antimitotic Agents
  作者：Siavosh Mahboobi、Herwig Pongratz、Harald Hufsky、Jörg Hockemeyer、Markus Frieser、Alexei Lyssenko、Dietrich H. Paper、Jutta Bürgermeister、Frank-D. Böhmer、Heinz-Herbert Fiebig、Angelika M. Burger、Silke Baasner、Thomas Beckers

  DOI：10.1021/jm010940+

  日期：2001.12.1

  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.
• 4- and 5-Aroylindoles as Novel Classes of Potent Antitubulin Agents
  作者：Jing-Ping Liou、Chang-Ying Wu、Hsing-Pang Hsieh、Chi-Yen Chang、Chi-Ming Chen、Ching-Chuan Kuo、Jang-Yang Chang

  DOI：10.1021/jm070557q

  日期：2007.9.1

  A novel series of 4- and 5-aroylindole derivatives was prepared and evaluated for antitumor activity. Several compounds showed excellent antiproliferative activity as inhibitors of tubulin polymerization. Compounds 13, 14, 15, and 18, with IC50 values of 1.9, 1.1, 1.2, and 1.8 mu M, respectively, exhibited more potent inhibition of tubulin polymerization than colchicine. They also displayed antiproliferative activity, with IC50 values ranging from 10 to 43 nM in a variety of human cell lines from different organs.