9-甲基-9H-咔唑-3-磺酰氯 | 905978-77-0

• 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
• 中文名称: 9-甲基-9H-咔唑-3-磺酰氯
• 英文名称: 9-methylcarbazole-3-sulfonyl chloride
• 英文别名: N-methyl-3-carbazolesulfonyl chloride；9-methyl-9H-carbazole-3-sulfonyl chloride
• CAS: 905978-77-0
• 化学式: C₁₃H₁₀ClNO₂S
• mdl: MFCD12912752
• 分子量: 279.747
• InChiKey: HUGGWTFEJQFFBF-UHFFFAOYSA-N

物化性质

• 沸点：
  392.5±24.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-甲基-9H-咔唑-3-磺酰氯 、 4-氯-2,5-二甲氧基苯胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以67%的产率得到N-(4-chloro-2,5-dimethoxyphenyl)-9-methyl-carbazole-3-sulfonamide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Carbazole Sulfonamides as a Novel Class of Antimitotic Agents Against Solid Tumors

  摘要：

  Two series of carbazole sulfonamides related to Combretastatin A4 (1) were synthesized and evaluated for antiproliferative activity. Thirteen of the 26 new sulfonamides exhibited IC50 values of < 1 AM against CEM leukemia cells. Five compounds were evaluated against a panel of eight human tumor cell lines. 9-Ethyl-N-(3,4,5-trimethoxyphenyl)-carbazole-3-sulfonamide (11a) showed significant antitumor activity in two human xenograft models (MCF-7 and Bel-7402). Preliminary studies with 11a showed that the mode of action involves arrest of M-phase cell cycle and induction of apoptosis by increasing expression of p53 and promoting bcl-2 phosphorylation. Unexpectedly, 11a only weakly inhibits tubulin polymerization, which suggests that the mode of action of 11a differs from 1 and involves an unidentified target(s). Also, the SAR information gleaned from ring A-substituted analogues varies significantly from that of 1. Carbazole sulfonamides are a novel promising class of antimitotic agents with clinical development potential.

  DOI：

  10.1021/jm060546h
• 作为产物：
  描述：

  N-甲基咔唑 在 氯磺酸 、 五氯化磷 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 9-甲基-9H-咔唑-3-磺酰氯
  参考文献：
  名称：

  Novel pyridinyl and pyrimidinylcarbazole sulfonamides as antiproliferative agents

  摘要：

  A series of azaheterocyclic carbazole sulfonamides was synthesized and evaluated for antiproliferative activity. The most potent compounds N-(2,6-dimethoxypyridine-3-yl)-9-ethyl and 9-methylcarbazole-3-sulfonamide (13 and 14) gave significant cytotoxicity (IC50 = 122 and 101 nM). Compound 13 displayed submicromolar activities against seven human tumor cell lines. The SARs of this series of sulfonamides which includes the influence of azaheterocycle rings, sulfonamide linkage, and the carbazole ring are described.

  DOI：

  10.1016/j.bmcl.2006.12.034

文献信息

• Preparation of Propargylic Sulfinates and their [2,3]-Sigmatropic Rearrangement to Allenic Sulfones
  作者：Rama Rao Tata、Carissa S. Hampton、Michael Harmata

  DOI：10.1002/adsc.201600986

  日期：2017.4.3

  scope of the [2,3]‐sigmatropic rearrangement of propargylic sulfinates to allenic sulfones by silver catalysis was expanded. A series of new propargylic sulfinate esters was generated from a variety of aromatic and heteroaromatic sulfonyl chlorides and their rearrangement to allenic sulfones is reported. In addition, the synthesis of propargylic sulfinate esters containing electron‐withdrawing benzenesulfonyl

  通过银催化，炔丙基亚磺酸盐[2,3]-σ重排为烯丙基砜的范围扩大了。从各种芳族和杂芳族磺酰氯生成了一系列新的炔丙基亚磺酸酯，并报道了它们被重排为烯丙基砜。此外，据报道含有吸电子的苯磺酰氯的炔丙基亚磺酸酯的合成。
• Synthesis and Structure−Activity Relationships of Carbazole Sulfonamides as a Novel Class of Antimitotic Agents Against Solid Tumors
  作者：Laixing Hu、Zhuo-rong Li、Yan Li、Jinrong Qu、Yi-He Ling、Jian-dong Jiang、David W. Boykin

  DOI：10.1021/jm060546h

  日期：2006.10.1

  Two series of carbazole sulfonamides related to Combretastatin A4 (1) were synthesized and evaluated for antiproliferative activity. Thirteen of the 26 new sulfonamides exhibited IC50 values of < 1 AM against CEM leukemia cells. Five compounds were evaluated against a panel of eight human tumor cell lines. 9-Ethyl-N-(3,4,5-trimethoxyphenyl)-carbazole-3-sulfonamide (11a) showed significant antitumor activity in two human xenograft models (MCF-7 and Bel-7402). Preliminary studies with 11a showed that the mode of action involves arrest of M-phase cell cycle and induction of apoptosis by increasing expression of p53 and promoting bcl-2 phosphorylation. Unexpectedly, 11a only weakly inhibits tubulin polymerization, which suggests that the mode of action of 11a differs from 1 and involves an unidentified target(s). Also, the SAR information gleaned from ring A-substituted analogues varies significantly from that of 1. Carbazole sulfonamides are a novel promising class of antimitotic agents with clinical development potential.
• Novel pyridinyl and pyrimidinylcarbazole sulfonamides as antiproliferative agents
  作者：Laixing Hu、Zhuo-rong Li、Yue-ming Wang、Yanbin Wu、Jian-Dong Jiang、David W. Boykin

  DOI：10.1016/j.bmcl.2006.12.034

  日期：2007.3

  A series of azaheterocyclic carbazole sulfonamides was synthesized and evaluated for antiproliferative activity. The most potent compounds N-(2,6-dimethoxypyridine-3-yl)-9-ethyl and 9-methylcarbazole-3-sulfonamide (13 and 14) gave significant cytotoxicity (IC50 = 122 and 101 nM). Compound 13 displayed submicromolar activities against seven human tumor cell lines. The SARs of this series of sulfonamides which includes the influence of azaheterocycle rings, sulfonamide linkage, and the carbazole ring are described.