1-(苯基磺酰基)-5-甲氧基-4-氮杂吲哚 | 372077-49-1

• 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: 1-(苯基磺酰基)-5-甲氧基-4-氮杂吲哚
• 中文别名: 5-甲氧基-1-(苯磺酰基)-1H-吡咯并[3,2-B]吡啶；1-(苯磺酰基)-5-甲氧基-4-氮杂吲哚
• 英文名称: 1-benzenesulfonyl-5-methoxy-1H-pyrrolo[3,2-b]pyridine
• 英文别名: 1-(Phenylsulfonyl)-5-methoxy-4-azaindole；1-(benzenesulfonyl)-5-methoxypyrrolo[3,2-b]pyridine
• CAS: 372077-49-1
• 化学式: C₁₄H₁₂N₂O₃S
• 分子量: 288.327
• InChiKey: DBGCFODVQKTQKT-UHFFFAOYSA-N

物化性质

• 熔点：
  128℃
• 沸点：
  474.1±48.0 °C(Predicted)
• 密度：
  1.34

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1-(苯基磺酰基)-5-甲氧基-4-氮杂吲哚 在 四甲基乙二胺 、 lithium diisopropyl amide 、 硼酸三甲酯 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 以95%的产率得到1-benzenesulfonyl-5-methoxy-1H-pyrrolo[3,2-b]pyridine-2-boronic acid
  参考文献：
  名称：

  方便获得C -2或C -5取代的4-氮杂吲哚衍生物

  摘要：

  N-苯磺酰基-4-氮杂吲哚1在C -2和C -5处的官能化是通过锂化反应和原始钯催化的化学反应进行的。这导致了非常有用的新的取代的4-氮杂吲哚衍生物的公平至高收率。

  DOI：

  10.1016/j.tet.2009.11.040
• 作为产物：
  描述：

  5-硝基-2-甲氧基吡啶 在 palladium on activated charcoal 、 苄基三乙基氯化铵 sodium hydroxide 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， -10.0~20.0 ℃ 、310.26 kPa 条件下， 反应 10.75h， 生成 1-(苯基磺酰基)-5-甲氧基-4-氮杂吲哚
  参考文献：
  名称：

  Preparation of 4-azaindole and 7-azaindole dimers with a bisalkoxyalkyl spacer in order to preferentially target melatonin MT1 receptors over melatonin MT2 receptors

  摘要：

  Several 4-azaindole and 7-azaindole dimer analogues of melatonin with a bisalkoxyalkyl spacer between the position 5 of each heterocycle were synthetized. Our aim was to investigate the influence of the spacers length on the selectivity of such compounds for the MT1 receptors over the MT2 receptors. Our results suggest the distance between indole ring seems to be an important parameter in determining the potency of binding with melatonin receptor site. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.03.005

文献信息

• AZAINDOLE DERIVATIVES WITH A COMBINATION OF PARTIAL NICOTINIC ACETYL-CHOLINE RECEPTOR AGONISM AND DOPAMINE REUPTAKE INHIBITION
  申请人：STOIT Axel

  公开号：US20080009514A1

  公开（公告）日：2008-01-10

  Azaindole derivatives of formula (I): wherein the symbols have the meanings given in the specification, are described. These compounds have a combination of partial nicotinic acetylcholine receptor agonism and dopamine reuptake inhibition. The invention also relates to pharmaceutical compositions containing these compounds, to methods for preparing them, methods for preparing novel intermediates useful for their synthesis, methods for preparing compositions, and uses of such compounds and compositions, for example, their use in administering them to patients to achieve a therapeutic effect in disorders in which nicotinic receptors and/or dopamine transporters are involved, or that can be treated via manipulation of those receptors

  阿扎因多ール衍生物的公式（I）如下： 其中符号的含义如说明书中所给。这些化合物具有部分尼古丁乙酰胆碱受体激动作用和去甲肾上腺素再摄取抑制作用。本发明还涉及包含这些化合物的药物组合物，制造它们的方法，制造用于其合成的新的中间体的方法，制造组合物的方法以及这些化合物和组合物的用途，例如，用于将它们施用于患者以在尼古丁受体和/或去甲肾上腺素转运体涉及的疾病中实现治疗效果，或者可以通过操纵这些受体来治疗的疾病。
• 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。
• 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.
• 2-ACYL-INDOLDERIVATE UND DEREN VERWENDUNG ALS ANTITUMORMITTEL
  申请人：Baxter Healthcare S.A.

  公开号：EP1276720B1

  公开（公告）日：2006-12-20
• AZAINDOLE DERIVATIVES WITH A COMBINATION OF PARTIAL NICOTINIC ACETYLCHOLINE RECEPTOR AGONISM AND DOPAMINE REUPTAKE INHIBITION
  申请人：Abbott Healthcare Products B.V.

  公开号：EP2041131B1

  公开（公告）日：2011-09-28