5-chloro-2-(3-nitrophenyl)-1,3-benzothiazole | 25284-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-2-(3-nitrophenyl)-1,3-benzothiazole
• 英文别名: 5-chloro-2-(3-nitrophenyl)-1,3-benzoxazole；5-chloro-2-(3-nitrophenyl)benzo[d]oxazole；2-(3-nitrophenyl)-5-chlorobenzoxazole；5-chloro-2-(3-nitro-phenyl)-benzooxazole；5-chloro-2-(3-nitrophenyl)benzoxazole
• CAS: 25284-12-2
• 化学式: C₁₃H₇ClN₂O₃
• 分子量: 274.663
• InChiKey: BZRKTCTVXNLZPL-UHFFFAOYSA-N

物化性质

• 熔点：
  184-186 °C
• 沸点：
  403.1±25.0 °C(Predicted)
• 密度：
  1.455±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(3-nitrophenyl)-1,3-benzothiazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 3.33h， 生成 N-[[3-(5-chloro-1,3-benzoxazol-2-yl)phenyl]carbamothioyl]-2-fluorobenzamide
  参考文献：
  名称：

  酰基硫脲对DUSP1抑制作用的合成及生物学评价。

  摘要：

  基于结构的虚拟筛选发现DUSP1抑制剂的尝试已产生了以苯并恶唑和酰基硫脲药效团为特征的支架。合成了一系列类似物以探索DUSP1抑制的结构活性关系（SAR）。

  DOI：

  10.1016/j.bmcl.2019.05.021
• 作为产物：
  描述：

  间硝基苯甲酰氯 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 5-chloro-2-(3-nitrophenyl)-1,3-benzothiazole
  参考文献：
  名称：

  2,3-Dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acid derivatives: a novel class of small molecule heparanase inhibitors

  摘要：

  A novel class of 2,3-dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acids are described as inhibitors of the endo-beta-glucuronidase heparanase. Several of the compounds, for example, 2-[4-propylamino-5-[5-(4-chloro)phenyl-benzoxazol-2-yl]phenyl]-2,3-dihydro-1,3-dioxo-IH-isoindole-5-carboxylic acid (9c), display potent heparanase inhibitory activity (IC50 200-500nM) and have high selectivity ( > 100-fold) over human beta-glucuronidase. They also show anti-angiogenic effects. Such compounds should serve as useful biological tools and may provide a basis for the design of novel therapeutic agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.086

文献信息

• Oxidative cyclization of thiophenolic and phenolic Schiff's bases promoted by PCC: a new oxidant for 2-substituted benzothiazoles and benzoxazoles
  作者：C. Praveen、K. Hemanth Kumar、D. Muralidharan、P.T. Perumal

  DOI：10.1016/j.tet.2008.01.004

  日期：2008.3

  Pyridinium chlorochromate (PCC) supported on silica gel effects the oxidative cyclization of structurally diverse thiophenolic and phenolic Schiff's bases, thereby providing an efficient and convenient method for the synthesis of a library of 2-arylbenzothiazoles and 2-arylbenzoxazoles.

  硅胶上负载的氯铬酸吡啶鎓（PCC）可以对结构多样的硫酚和酚Schiff碱进行氧化环化，从而为合成2-芳基苯并噻唑和2-芳基苯并恶唑的库提供了一种高效便捷的方法。
• Microwave-assisted one-pot synthesis of benzothiazole and benzoxazole libraries as analgesic agents
  作者：C PRAVEEN、A NANDAKUMAR、P DHEENKUMAR、D MURALIDHARAN、P T PERUMAL

  DOI：10.1007/s12039-012-0251-3

  日期：2012.5

  Microwave-assisted synthesis of benzothiazole and benzoxazole libraries via PIFA promoted cyclocondensation of 2-aminothiophenols/2-aminophenols with aldehydes under one-pot condition in good to excellent yields was achieved. Twenty compounds have been investigated for their analgesic activity and showed moderate to good activity.

  通过一锅法条件下，利用PIFA促进的2-氨基硫酚/2-氨基酚与醛的环化缩合反应，实现了苯并噻唑和苯并噁唑库的微波辅助合成，产率良好至优秀。对二十个化合物进行了镇痛活性研究，显示出中等至良好的活性。
• KMnO4/HOAc system promoted one-pot synthesis of benzoxazoles from o-aminophenols or oxidative cyclization of o-hydroxyarylidene anilines at room temperature
  作者：B. F. Mirjalili、A. Bamoniri、E. Bagheri

  DOI：10.1007/s13738-015-0795-5

  日期：2016.5

  1,3-Benzoxazoles via oxidative cyclization of corresponding o-hydroxyarylidene anilines was synthesized in the presence of KMnO4/HOAc system. This system also was applied for the one-pot synthesis of 1,3-benzoxazoles from o-amino phenols and aldehydes. The both protocols were processed at room temperature under solvent-free conditions with good to excellent yields.

  在KMnO4/HOAc体系的存在下，通过相应的o-羟基芳基亚胺的氧化环化合成了1,3-苯并恶唑。这一体系还用于从o-氨基酚和醛的一锅法合成1,3-苯并恶唑。这两种方法均在室温下无溶剂条件下进行，产率良好至优秀。
• Trois nouvelles voies de synthèse des dérivés 1,3-azoliques sous micro-ondes
  作者：Khalid Bougrin、André Loupy、Mohamed Soufiaoui

  DOI：10.1016/s0040-4020(98)00431-1

  日期：1998.7

  Three new ways to synthesize 1,3 - azoles derivatives on mineral supports using or or by fusion “in dry media” are described. The reactions are activated under microwave irradiation in a monomode Synthewave 402 reactor. The reaction times are considerably shortened and the products are obtained in higher yields and better purity, than compared to conventional heating.

  描述了使用“或在干燥介质中”或通过融合在矿物载体上合成1,3-唑类衍生物的三种新方法。在单模Synthewave 402反应器中在微波辐射下激活反应。与常规加热相比，反应时间大大缩短，并且以更高的收率和更好的纯度获得了产物。
• Benzoxazoles Useful in the Treatment of Inflammation
  申请人：Pelcman Benjamin

  公开号：US20090258917A1

  公开（公告）日：2009-10-15

  There is provided the use of a compound of formula I, wherein Y, W 1 to W 4 , Z 1 to Z 4 and R have meanings given in the description, and pharmaceutically-acceptable salts thereof, for the manufacture of a medicament for the treatment of a disease in which inhibition of the activity of a member of the MAPEG family is desired and/or required, and particularly in the treatment of inflammation.

  本发明提供了使用式I的化合物及其药学上可接受的盐的制备药物，用于治疗需要或希望抑制MAPEG家族成员活性的疾病，尤其是治疗炎症。其中，Y，W1至W4，Z1至Z4和R的含义详见说明书。