2-(4-hydroxy-3-nitrophenyl)benzothiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxy-3-nitrophenyl)benzothiazole
• 英文别名: 4-(benzo[d]thiazol-2-yl)-2-nitrophenol；4-(2-benzothiazolyl)-2-nitrophenol；4-(1,3-benzothiazol-2-yl)-2-nitrophenol
• 化学式: C₁₃H₈N₂O₃S
• 分子量: 272.284
• InChiKey: LXSUPDDEYFDPFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxy-3-nitrophenyl)benzothiazole 在 sodium tetrahydroborate 、 copper diacetate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 36.0h， 生成 C₁₅H₁₄N₂O₂S
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of rhenium 2-arylbenzothiazoles as β-amyloid plaque binding agents

  摘要：

  To continue our efforts toward the development of Tc-99m PiB analogs, we have synthesized 24 neutral and lipophilic Re (as a surrogate of Tc-99m) 2-arylbenzothiazoles, and explored their structure-activity relationship for binding to A beta(1-40) fibrils. These Re complexes were designed and synthesized via the integrated approach, so their 99mTc analogs would have a greater chance of crossing the blood-brain barrier. While the lipophilicities (logP(C18) = 1.59-3.53) of these Re 2-arylbenzothiazoles were all within suitable range, their binding affinities (K-i = 30-617 nM) to A beta(1-40) fibrils varied widely depending on the selection and integration of the tetradentate chelator into the 2-phenylbenzothiazole pharmacophore. For potential clinical applications, further refinement to obtain Re 2-arylbenzothiazoles with better binding affinities (<10 nM) will likely be needed. The integrated approach reported here to generate compact, neutral and lipophilic Re 2-arylbenzothiazoles could be applied to other potent pharmacophores as well to convert other current Ab PET tracers to their Tc-99m analogs for more widespread application via the use of SPECT scanners. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.068
• 作为产物：
  描述：

  4-(1,3-苯并噻唑-2-基)苯酚 在 sodium nitrate 、 硫酸 作用下， 反应 3.0h， 以35.98%的产率得到2-(4-hydroxy-3-nitrophenyl)benzothiazole
  参考文献：
  名称：

  Nam, Nguyen Hai; Dung, Phan Thi Phuong; Thuong, Phuong Thien, Medicinal Chemistry, 2011, vol. 7, # 2, p. 127 - 134

  摘要：

  DOI：

文献信息

• Heterocyclic substituted-phenoxyalkylisoxazoles as antiviral useful
  申请人：Sterling Drug Inc.

  公开号：US04857539A1

  公开（公告）日：1989-08-15

  Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms; Z is N or HC; R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl; R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and Het is selected from specified heterocyclic groups, are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  化合物的公式为##STR1##其中：Y是3-9个碳原子的烷基桥；Z是N或HC；R是氢或1-5个碳原子的低烷基，但当Z是N时，R是低烷基；R.sub.1和R.sub.2是氢、卤素、低烷基、低烷氧基、硝基、低烷氧羰基或三氟甲基；Het从指定的杂环基团中选择，对抗病毒剂，特别是对抗小RNA病毒，包括多种鼻病毒菌株。
• A ball-milling strategy for the synthesis of benzothiazole, benzimidazole and benzoxazole derivatives under solvent-free conditions
  作者：Hemant Sharma、Narinder Singh、Doo Ok Jang

  DOI：10.1039/c4gc01142b

  日期：——

  A convenient solvent-free method for the synthesis of benzothiazole, benzimidazole, and benzoxazole derivatives has been developed using recyclable ZnO-NPs via a ball-milling strategy. The method affords environmentally friendly reaction conditions that score high on the ecoscale with the low E-factor. The process is also highly efficient even on a multi-gram scale and provides easy product isolation

  通过球磨策略，使用可回收的ZnO-NP ，开发了一种方便的无溶剂合成苯并噻唑，苯并咪唑和苯并恶唑衍生物的方法。该方法提供了对环境友好的反应条件，该条件在生态规模上得分很高，而E因子却很低。该过程即使在几克规模的情况下也非常高效，并且可以轻松实现产品隔离。
• Thiazolylphenoxyalkylisoxazoles, related compounds, and their use as
  申请人：Sterling Drug Inc.

  公开号：US05051437A1

  公开（公告）日：1991-09-24

  Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms; Z is N or HC; R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl; R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; and Het is selected from thiazole, benzothiazole and benzoxazole groups, are useful as antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.

  式为##STR1##的化合物，其中：Y是3-9个碳原子的烷基桥；Z为N或HC；R为氢或1-5个碳原子的低烷基，但当Z为N时，R为低烷基；R.sub.1和R.sub.2为氢、卤素、低烷基、低烷氧基、硝基、低烷氧羰基或三氟甲基；Het选自噻唑、苯并噻唑和苯并噁唑基团，可用作抗病毒剂，特别是对抗多种鼻病毒菌株的畏克病毒。
• 2-Aminophenol derivatives and process for their preparation
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0083204A2

  公开（公告）日：1983-07-06

  2-AMINOPHENOL derivatives of the general formula: [wherein R represents a group of the general formula: (in which Z represents a sulfur atom or a sulfinyl group and (R1)n represents that: (i) n is an integer of 1, 2 or 3 and R1, which may be the same or different, is a hydrogen atom, a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms or a halogen atom; (ii) n is an integer of 1, 2 or 3 and R' is a hydroxy group; or (iii) n is an integer of 2 and two R's are a hydroxy group and an amino group, a hydroxy group and a straight-or branched-chain alkyl group containing from 1 to 6 carbon atoms, or a hydroxy group and a halogen atom, such groups being at o-position or p-position to each other), or R represents a group of the general formula: (in which m is an integer of 1 or 2 and R2, which may be the same or different, represents a hydrogen atom, a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms or a halogen atom), or R represents a group of the general formula: (in which the various symbols are as hereinbefore defined), or R represents a group of the general formula:

  通式如下的 2-氨基苯酚衍生物 [其中 R 代表通式如下的基团 (其中 Z 代表硫原子或亚磺酰基，(R1)n 代表： (i) n 是 1、2 或 3 的整数，R1（可以相同或不同）是氢原子、含有 1 至 6 个碳原子的直链或支链烷基或卤素原子； (ii) n 是 1、2 或 3 的整数，R' 是羟基；或 (iii) n 为 2 的整数，且两个 R 分别为羟基和氨基、羟基和含 1 至 6 个碳原子的直链或支链烷基，或羟基和卤素原子，这些基团互为 o 位或 p 位），或 R 代表通式如下的基团 (其中 m 是 1 或 2 的整数，R2（可以相同或不同）代表氢原子、含有 1 至 6 个碳原子的直链或支链烷基或卤素原子），或 R 代表通式如下的基团： (其中各符号如前定义），或 R 代表通式如下的基团：
• Heterocyclic substituted-phenoxyalkyl-isoxazoles and-furans, their preparation and use as antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0207453A2

  公开（公告）日：1987-01-07

  Compounds of the formula are disclosed, wherein: Y is an alkylene bridge of 3-9 carbon atoms; Z is N or HC; R is hydrogen or lower-alkyl of 1-3 carbon atoms, with the proviso that when Z is N, R is lower-alkyl; R1 and R2 are each hydrogen, halogen, methyl, nitro, lower-alkoxycarbonyl or trifluoromethyl; and Het is a heterocyclic group, and pharmaceutically acceptable acid addition salts thereof, as well as methods for preparation and use thereof. The compounds exhibit valuable antiviral properties.

  公开了式 公开了式 Y 是 3-9 个碳原子的亚烷基桥； Z 是 N 或 HC R 是氢或 1-3 个碳原子的低级烷基，但当 Z 是 N 时，R 是低级烷基； R1 和 R2 分别是氢、卤素、甲基、硝基、低级烷氧基羰基或三氟甲基；以及 Het 是杂环基团，及其药学上可接受的酸加成盐，以及其制备和使用方法。这些化合物具有宝贵的抗病毒特性。