2-氨基萘并o[1,2-d][1,3]噻唑-5-醇 | 26269-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并噻唑类
• 中文名称: 2-氨基萘并o[1,2-d][1,3]噻唑-5-醇
• 英文名称: 2-aminonaphtho[1,2-d]thiazol-5-ol
• 英文别名: 2-amino-naphtho[1,2-d]thiazol-5-ol；2-Amino-5-hydroxynaphtho-<1,2-d>thiazole；Naphtho[1,2-d]thiazol-5-ol, 2-amino-；2-aminobenzo[e][1,3]benzothiazol-5-ol
• CAS: 26269-04-5
• 化学式: C₁₁H₈N₂OS
• 分子量: 216.263
• InChiKey: XRWMHTFOPYEGAG-UHFFFAOYSA-N

物化性质

• 沸点：
  492.1±37.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 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：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-氨基萘并o[1,2-d][1,3]噻唑-5-醇 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide
  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
• 作为产物：
  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

• Anti-malarial compounds, compositions and methods
  申请人：——

  公开号：US20030186993A1

  公开（公告）日：2003-10-02

  The present invention is directed to substituted naphthothiazolium, aromatic guanylhydrazones, and other compounds and compositions with anti-malarial activity useful for the treatment and prophylaxis of malaria. The compounds are provided for the treatment of malaria or the sequelae of malarial infection, for depolymerizing malaria pigment (hemozoin), and for ameliorating the adverse effects of hemozoin on host cells.

  本发明涉及替代萘并噻唑、芳香基胍脲和其他具有抗疟活性的化合物和组合物，适用于治疗和预防疟疾。这些化合物可用于治疗疟疾或疟疾感染的后遗症，用于降解疟原色素（血红素），并用于改善疟原色素对宿主细胞的不良影响。
• Benzothiazole derivative, its use, and pharmaceutical compositions comprising it
  申请人：Eisai Co., Ltd.

  公开号：EP0295656A1

  公开（公告）日：1988-12-21

  A benzothiazole compound having the formula below and pharmaceutical compositions containing it are disclosed which are effective to inhibit the production of leukotriene. The compounds can be used for the making of medicaments effective against allergy, asthma, affections of the skin, allergic rhinitis and affection of a cardiovascular system, in which R20 is ester or amide and -NR5R6 is amino in variety.

  本发明公开了一种具有下式的苯并噻唑化合物和含有该化合物的药物组合物，它们能有效抑制白三烯的生成。该化合物可用于制造对过敏、哮喘、皮肤病、过敏性鼻炎和心血管系统疾病有效的药物、 其中 R20 是酯或酰胺，-NR5R6 是各种氨基。
• Reaction of quinones with thiourea. Novel route to 2-amino-6-hydroxybenzothiazoles and 2-amino-5-hydroxynaphtho[1,2-d] thiazoles
  作者：Philip T. S. Lau、T. E. Compf

  DOI：10.1021/jo00837a003

  日期：1970.12
• 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.
• Benzothiazole derivative
  申请人：Eisai Co., Ltd.

  公开号：EP0507318B1

  公开（公告）日：1997-09-10