5-hydroxynaphtho[1,2-d]thiazol-2-aminium chloride | 26269-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并噻唑类
• 英文名称: 5-hydroxynaphtho[1,2-d]thiazol-2-aminium chloride
• 英文别名: 2-amino-naphtho[1,2-d]thiazol-5-ol; hydrochloride；2-Aminobenzo[e][1,3]benzothiazol-1-ium-5-ol;chloride
• CAS: 26269-03-4
• 化学式: C₁₁H₈N₂OS*ClH
• 分子量: 252.724
• InChiKey: WHWSRVLNUYCTSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxynaphtho[1,2-d]thiazol-2-aminium chloride 在 ammonium hydroxide 作用下， 以 水 为溶剂， 以94%的产率得到2-氨基萘并o[1,2-d][1,3]噻唑-5-醇
  参考文献：
  名称：

  5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes

  摘要：

  3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2'-binaphthothiazole]-1,1'-diol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.043

文献信息

• Method and composition for rejuvinating cells, tissues organs, hair and nails
  申请人：——

  公开号：US20020188015A1

  公开（公告）日：2002-12-12

  In one embodiment, the present invention relates to compounds and compositions including pharmaceutical compositions containing the compounds and associated methods that uncouple sugar-mediated coupling of proteins, lipids, nucleic acids, and other biomaterials, and any combination thereof. In another embodiment, the compositions and associated methods have utility in vivo to reduce the deleterious effects of sugar-mediated coupling processes in an organism, when the organism is exposed to the compound or composition internally, by ingestion, transdermal application, or other means. In yet another embodiment, the compositions and associated methods are useful for the ex-vivo treatment of organs, cells and tissues and external treatment of hair, nails and skin to rejuvenate them by changing deformability and increase the tissue diffusion coefficient. In a further embodiment, the present invention relates to novel compounds and pharmaceutical compositions.

  在一个实施例中，本发明涉及包含药物组合物的化合物和组合物，其中药物组合物包含这些化合物，并且相关方法解耦蛋白质、脂质、核酸和其他生物材料以及它们的任意组合的糖介导偶联。在另一个实施例中，这些组合物和相关方法在体内具有实用性，用于减少生物体暴露于内部摄入、经皮应用或其他方式的化合物或组合物时，糖介导偶联过程的有害影响。在另一个实施例中，这些组合物和相关方法对器官、细胞和组织的离体处理以及头发、指甲和皮肤的外部处理具有用处，通过改变可变性和增加组织扩散系数来使它们恢复活力。在另一个实施例中，本发明涉及新颖的化合物和药物组合物。
• Synthesis, Cytotoxicity and<i>In Vitro</i>Antileishmanial Activity of Naphthothiazoles
  作者：Juliano S. de Toledo、Paulo E. S. Junior、Viviane Manfrim、Camila F. Pinzan、Alexandre S. de Araujo、Angela K. Cruz、Flavio S. Emery

  DOI：10.1111/cbdd.12123

  日期：2013.6

  The leishmaniasis is a spectral disease caused by the protozoan Leishmania spp., which threatens millions of people worldwide. Current treatments exhibit high toxicity, and there is no vaccine available. The need for new lead compounds with leishmanicidal activity is urgent. Considering that many lead leishmanicidal compounds contain a quinoidal scaffold and the thiazole heterocyclic ring is found in a number of antimicrobial drugs, we proposed a hybridization approach to generate a diverse set of semi‐synthetic heterocycles with antileishmanial activity. We found that almost all synthesized compounds demonstrated potent activity against promastigotes of Leishmania (Viannia) braziliensis and reduced the survival index of Leishmania amastigotes in mammalian macrophages. Furthermore, the compounds were not cytotoxic to macrophages at fivefold higher concentrations than the EC50 for promastigotes. All molecules fulfilled Lipinski's Rule of Five, which predicts efficient orally absorption and permeation through biological membranes, the in silico pharmacokinetic profile confirmed these characteristics. The potent and selective activity of semi‐synthetic naphthothiazoles against promastigotes and amastigotes reveals that the 2‐amino‐naphthothiazole ring may represent a scaffold for the design of compounds with leishmanicidal properties and encourage the development of drug formulation and new compounds for further studies in vivo.
• US6777557B2
  申请人：——

  公开号：US6777557B2

  公开（公告）日：2004-08-17
• US7022721B1
  申请人：——

  公开号：US7022721B1

  公开（公告）日：2006-04-04
• 5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes
  作者：Stuart Aiken、Ben Allsopp、Kathryn Booth、Christopher D. Gabbutt、B. Mark Heron、Craig R. Rice

  DOI：10.1016/j.tet.2014.10.043

  日期：2014.12

  3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2'-binaphthothiazole]-1,1'-diol. (C) 2014 Elsevier Ltd. All rights reserved.