5'-chloro-spiro[benzothiazole-2(3H),3'-[3H]indol]-2'(1'H)-one | 1220999-67-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5'-chloro-spiro[benzothiazole-2(3H),3'-[3H]indol]-2'(1'H)-one
• 英文别名: 5'-chloro-3H-spiro[benzo[d]thiazole-2,3'-indolin]-2'-one；5'-chloro-3H-spiro[1,3-benzothiazole-2,3'-indol]-2'(1'H)-one；5-chloro-3-(indolin-2-one)benzothiazoline；5-chlorospiro[1H-indole-3,2'-3H-1,3-benzothiazole]-2-one
• CAS: 1220999-67-6
• 化学式: C₁₄H₉ClN₂OS
• 分子量: 288.757
• InChiKey: BGIQDZYSSRBQDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-chloro-spiro[benzothiazole-2(3H),3'-[3H]indol]-2'(1'H)-one 、 palladium dichloride 在 NH₃ 作用下， 以 甲醇 、 水 为溶剂， 生成 [Pd(5-chloro-3-(indolin-2-one)benzothiazoline)2]
  参考文献：
  名称：

  Palladium(II) and platinum(II) derivatives of benzothiazoline ligands: Synthesis, characterization, antimicrobial and antispermatogenic activity

  摘要：

  A series of Pd(II) and Pt(II) complexes with two NS donor ligands, 5-chloro-3-(indolin-2-one)benzothiazoline and 6-nitro-3-(indolin-2-one)benzothiazoline, have been synthesized by the reaction of metal chlorides (PdCl2 and PtCl2) with ligands in 1:2 molar ratios. All the synthesized compounds were characterized by elemental analyses, melting point determinations and a combination of electronic, IR, H-1 NMR and C-13 NMR spectroscopic techniques for structure elucidation. In order to evaluate the effect of metal ions upon chelation, both the ligands and their complexes have been screened for their antimicrobial activity against the various pathogenic bacterial and fungal strains. The metal complexes have shown to be more antimicrobial against the microbial species as compared to free ligands. One of the ligands, 5-chloro-3-(indolin-2-one)benzothiazoline and its corresponding palladium and platinum complexes have been tested for their antifertility activity in male albino rats. The marked reduction in sperm motility and density resulted in infertility by 62-90%. Significant alterations were found in biochemical parameters of reproductive organs in treated animals as compared to control group. It is concluded that all these effects may finally impair the fertility of male rats. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.08.076
• 作为产物：
  描述：

  5-氯吲哚 在 氧气 、 孟加拉红内酯 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 5'-chloro-spiro[benzothiazole-2(3H),3'-[3H]indol]-2'(1'H)-one
  参考文献：
  名称：

  吲哚和吡咯的可见光介导的脱芳香化作用，以制得药品和农药。

  摘要：

  借助于可见光和氧气已经实现了吲哚衍生物向相应的靛红衍生物的脱芳香化作用。应该注意的是，对于合成药物和生物活性化合物而言，伊斯汀衍生物非常重要。值得注意的是，这种化学方法与N保护和无保护的吲哚均具有出色的表现。另外，该方法还可以应用于在单个步骤中对吡咯衍生物进行脱芳香化以生成环状酰亚胺。后来，这种方法学被用于合成四种药物和一种名为双硫毒素B的农药。详细的机理研究揭示了氧气和光催化剂的实际作用。

  DOI：

  10.1002/chem.201904168

文献信息

• Camphor sulfonic acid catalyzed a simple, facile, and general method for the synthesis of 2-arylbenzothiazoles, 2-arylbenzimidazoles, and 3<i>H</i>-spiro[benzo[<i>d</i>]thiazole-2,3′-indolin]-2′-ones at room temperature
  作者：Gurpreet Kaur、Radha Moudgil、Mussarat Shamim、Vivek Kumar Gupta、Bubun Banerjee

  DOI：10.1080/00397911.2020.1870043

  日期：2021.4.3

  developed for the synthesis of structurally diverse 2-arylbenzothiazole derivatives from the reactions of 2-aminothiophenol and various aromatic aldehydes using camphor sulfonic acid a low cost, commercially available, efficient organo-catalyst in aqueous ethanol at room temperature. Under the same optimized conditions, a series of 2-arylbenzimidazoles was also synthesized starting from o-phenylenediamines

  摘要 已经开发了一种简单，温和，环保，通用且方便的方法，用于使用樟脑磺酸由2-氨基硫酚与各种芳香醛的反应合成结构多样的2-芳基苯并噻唑衍生物，这是一种低成本，可商购，高效的方法。有机催化剂在室温下于乙醇水溶液中。在相同的优化条件下，还从邻苯二胺和各种醛开始合成了一系列的2-芳基苯并咪唑，而合成了3 H-螺[苯并[ d ]噻唑-2,3'-吲哚] -2'-一个。由2-氨基苯硫酚和取代的靛红的反应完成。
• Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents
  作者：Nilgün Karalı、Özlen Güzel、Nurten Özsoy、Süheyla Özbey、Aydın Salman

  DOI：10.1016/j.ejmech.2009.12.001

  日期：2010.3

  3H-Spiro[1,3-benzothiazole-2,3'-indol]-2'(1',H)-ones 3a-c and 4a-e were synthesized from treating the 5-substituted 1H-indole-2,3-diones with 2-aminothiophenol in ethanol. The structures were confirmed by elemental analyses, spectrometry (IR, H-1 NMR, C-13 NMR, HSQC-2D and LCMS-APCI) and single crystal X-ray analysis. The new compounds were screened for their antioxidant activities such as the Fe3+/ ascorbate system induced inhibition of lipid peroxidation (LP) in liposomes, trolox equivalent antioxidant capacity (TEAC), scavenging effect on diphenylpicryl hydrazine (DPPH center dot), and reducing power. These compounds showed potent scavenging activities against DPPH center dot and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS(center dot+)) radicals, reducing powers, and strong inhibitory capacity on lipid peroxidation. Compound 4a incorporating methyl both at R-1 and R-2 was found to be the most potent antioxidant described in this study. Compounds 3b and 4b were selected as representative compounds by the National Cancer Institute for screening against anticancer activity and these compounds were found to be cytotoxic against CNS cancer cell line SNB-75 in the primary Screen. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Visible‐Light‐Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides
  作者：Waldemar Schilling、Yu Zhang、Daniel Riemer、Shoubhik Das

  DOI：10.1002/chem.201904168

  日期：2020.1.7

  Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied

  借助于可见光和氧气已经实现了吲哚衍生物向相应的靛红衍生物的脱芳香化作用。应该注意的是，对于合成药物和生物活性化合物而言，伊斯汀衍生物非常重要。值得注意的是，这种化学方法与N保护和无保护的吲哚均具有出色的表现。另外，该方法还可以应用于在单个步骤中对吡咯衍生物进行脱芳香化以生成环状酰亚胺。后来，这种方法学被用于合成四种药物和一种名为双硫毒素B的农药。详细的机理研究揭示了氧气和光催化剂的实际作用。
• Palladium(II) and platinum(II) derivatives of benzothiazoline ligands: Synthesis, characterization, antimicrobial and antispermatogenic activity
  作者：Krishna Sharma、R.V. Singh、Nighat Fahmi

  DOI：10.1016/j.saa.2010.08.076

  日期：2011.1

  A series of Pd(II) and Pt(II) complexes with two NS donor ligands, 5-chloro-3-(indolin-2-one)benzothiazoline and 6-nitro-3-(indolin-2-one)benzothiazoline, have been synthesized by the reaction of metal chlorides (PdCl2 and PtCl2) with ligands in 1:2 molar ratios. All the synthesized compounds were characterized by elemental analyses, melting point determinations and a combination of electronic, IR, H-1 NMR and C-13 NMR spectroscopic techniques for structure elucidation. In order to evaluate the effect of metal ions upon chelation, both the ligands and their complexes have been screened for their antimicrobial activity against the various pathogenic bacterial and fungal strains. The metal complexes have shown to be more antimicrobial against the microbial species as compared to free ligands. One of the ligands, 5-chloro-3-(indolin-2-one)benzothiazoline and its corresponding palladium and platinum complexes have been tested for their antifertility activity in male albino rats. The marked reduction in sperm motility and density resulted in infertility by 62-90%. Significant alterations were found in biochemical parameters of reproductive organs in treated animals as compared to control group. It is concluded that all these effects may finally impair the fertility of male rats. (C) 2010 Elsevier B.V. All rights reserved.