sodium 2-amino-5-chlorothiophenolate | 116034-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: sodium 2-amino-5-chlorothiophenolate
• 英文别名: Sodium;2-amino-5-chlorobenzenethiolate
• CAS: 116034-04-9
• 化学式: C₆H₅ClNS*Na
• 分子量: 181.621
• InChiKey: RDLFOEABSOXLSM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.17
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium 2-amino-5-chlorothiophenolate 在 吡啶 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (4-chloro-2-cyanomethylsulfanylphenyl)carbamic acid ethyl ester
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide and N-(2-cyanomethylsulfonylphenyl)acylamide derivatives as potential activators of ATP sensitive potassium channels

  摘要：

  1, 2,4-Thiadiazine derivatives, like 3-methyl-7-chlorobenzo-4H-1,2,4-thiadiazine 1,1-dioxide, diazoxide and 7-chloro-3-isopropylamino-4H-benzo-1,2,4-thiadiazine 1,1-dioxide, BPDZ 73, are potent openers of Kir6.2/SUR1 K-ATP channels. To explore the structure-activity relationship of this series of K-ATP openers, 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide and N-(2-cyano-methylsulfonylphenyl)acylamide derivatives were synthesized from 2-acetylamino-5-chloro-benzenesulfonic acid pyridinium salt or 2-aminobenzenethiols. The 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide derivatives (e.g., 7-chloro-3-isopropylamino-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide, 3f) were found to activate K-ATP channels as indicated by their ability to hyperpolarize beta cell membrane potential, to inhibit glucose-stimulated insulin release in vitro and to increase ion currents through Kir6.2/SUR1 channel as measured by patch clamp. The potency and efficacy of, for example, 3f is however significantly reduced compared to the corresponding 4H-1,2,4-benzothiadiazine 1,1-dioxide derivatives. Opening of the 4H-1,2,4-thiadiazine ring to get (e.g., 2-cyanomethylsulfonyl-4-fluorophenyl) carbamic acid isopropyl ester (4c) gives rise to compounds, which are able to open K-ATP channels but with considerable reduced potency compared to, for example, diazoxide. Compound 3a, 7-chloro-3-methyl-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide, which inhibits insulin release in vitro from beta cells and rat islets, reduces plasma insulin levels and blood pressure in anaesthetized rats upon intravenous administration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.051
• 作为产物：
  描述：

  2-氨基-6-氯苯并噻唑 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.5h， 生成 sodium 2-amino-5-chlorothiophenolate
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide and N-(2-cyanomethylsulfonylphenyl)acylamide derivatives as potential activators of ATP sensitive potassium channels

  摘要：

  1, 2,4-Thiadiazine derivatives, like 3-methyl-7-chlorobenzo-4H-1,2,4-thiadiazine 1,1-dioxide, diazoxide and 7-chloro-3-isopropylamino-4H-benzo-1,2,4-thiadiazine 1,1-dioxide, BPDZ 73, are potent openers of Kir6.2/SUR1 K-ATP channels. To explore the structure-activity relationship of this series of K-ATP openers, 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide and N-(2-cyano-methylsulfonylphenyl)acylamide derivatives were synthesized from 2-acetylamino-5-chloro-benzenesulfonic acid pyridinium salt or 2-aminobenzenethiols. The 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide derivatives (e.g., 7-chloro-3-isopropylamino-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide, 3f) were found to activate K-ATP channels as indicated by their ability to hyperpolarize beta cell membrane potential, to inhibit glucose-stimulated insulin release in vitro and to increase ion currents through Kir6.2/SUR1 channel as measured by patch clamp. The potency and efficacy of, for example, 3f is however significantly reduced compared to the corresponding 4H-1,2,4-benzothiadiazine 1,1-dioxide derivatives. Opening of the 4H-1,2,4-thiadiazine ring to get (e.g., 2-cyanomethylsulfonyl-4-fluorophenyl) carbamic acid isopropyl ester (4c) gives rise to compounds, which are able to open K-ATP channels but with considerable reduced potency compared to, for example, diazoxide. Compound 3a, 7-chloro-3-methyl-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide, which inhibits insulin release in vitro from beta cells and rat islets, reduces plasma insulin levels and blood pressure in anaesthetized rats upon intravenous administration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.051

文献信息

• Synthesis of 10-(4-methyl-1-piperazinyl)thieno[3,2-<i>b</i>][1,5]benzothiazepines
  作者：Carlos Corral、Ana Lasso、Jaime Lissavetzky、Ana M. Valdeolmillos

  DOI：10.1002/jhet.5570220541

  日期：1985.9

  A series of the title compounds has been synthesized by two alternative methods in order to study their potential neuroleptical activity and to compare it with the pharmacological data already obtained for compounds of other isomeric or related series.

  为了研究其潜在的神经病学活性并将其与已经获得的其他异构体或相关系列化合物的药理数据进行比较，已通过两种替代方法合成了一系列标题化合物。
• Process for the preparation of thiazine-indigo compounds and of new intermediates therefor
  申请人：Clariant Finance (BVI) Limited

  公开号：EP1036821A1

  公开（公告）日：2000-09-20

  New heterocyclic compounds are disclosed which are used as intermediates for the preparation of trans-thiazine-indigo pigments which are in part new compounds and can be used for the mass pigmentation of organic substrates. Also disclosed are different environmentally friendly water-based processes for the preparation of the new heterocyclic compounds and the corresponding pigments.

  本发明公开了新的杂环化合物，这些化合物可用作制备反式噻嗪-靛蓝颜料的中间体，而反式噻嗪-靛蓝颜料部分属于新化合物，可用于有机基质的大量着色。此外，还公开了制备新杂环化合物和相应颜料的不同环保型水基工艺。
• US6339084B1
  申请人：——

  公开号：US6339084B1

  公开（公告）日：2002-01-15
• US6472527B1
  申请人：——

  公开号：US6472527B1

  公开（公告）日：2002-10-29
• Synthesis and pharmacological evaluation of 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide and N-(2-cyanomethylsulfonylphenyl)acylamide derivatives as potential activators of ATP sensitive potassium channels
  作者：Søren C. Schou、Holger C. Hansen、Tina M. Tagmose、Harrie C.M. Boonen、Anne Worsaae、Michael Drabowski、Philip Wahl、Per O.G. Arkhammar、Thora Bodvarsdottir、Marie-Hélène Antoine、Philippe Lebrun、John Bondo Hansen

  DOI：10.1016/j.bmc.2004.09.051

  日期：2005.1

  1, 2,4-Thiadiazine derivatives, like 3-methyl-7-chlorobenzo-4H-1,2,4-thiadiazine 1,1-dioxide, diazoxide and 7-chloro-3-isopropylamino-4H-benzo-1,2,4-thiadiazine 1,1-dioxide, BPDZ 73, are potent openers of Kir6.2/SUR1 K-ATP channels. To explore the structure-activity relationship of this series of K-ATP openers, 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide and N-(2-cyano-methylsulfonylphenyl)acylamide derivatives were synthesized from 2-acetylamino-5-chloro-benzenesulfonic acid pyridinium salt or 2-aminobenzenethiols. The 4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide derivatives (e.g., 7-chloro-3-isopropylamino-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide, 3f) were found to activate K-ATP channels as indicated by their ability to hyperpolarize beta cell membrane potential, to inhibit glucose-stimulated insulin release in vitro and to increase ion currents through Kir6.2/SUR1 channel as measured by patch clamp. The potency and efficacy of, for example, 3f is however significantly reduced compared to the corresponding 4H-1,2,4-benzothiadiazine 1,1-dioxide derivatives. Opening of the 4H-1,2,4-thiadiazine ring to get (e.g., 2-cyanomethylsulfonyl-4-fluorophenyl) carbamic acid isopropyl ester (4c) gives rise to compounds, which are able to open K-ATP channels but with considerable reduced potency compared to, for example, diazoxide. Compound 3a, 7-chloro-3-methyl-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxide, which inhibits insulin release in vitro from beta cells and rat islets, reduces plasma insulin levels and blood pressure in anaesthetized rats upon intravenous administration. (C) 2004 Elsevier Ltd. All rights reserved.