1-(benzo[d]thiazol-2-ylamino)(4-(dimethylamino)phenyl)-naphthalen-2-ol | 1616917-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(benzo[d]thiazol-2-ylamino)(4-(dimethylamino)phenyl)-naphthalen-2-ol
• 英文别名: 1-[(1,3-Benzothiazol-2-ylamino)-[4-(dimethylamino)phenyl]methyl]naphthalen-2-ol；1-[(1,3-benzothiazol-2-ylamino)-[4-(dimethylamino)phenyl]methyl]naphthalen-2-ol
• CAS: 1616917-46-4
• 化学式: C₂₆H₂₃N₃OS
• 分子量: 425.554
• InChiKey: CEKDOJDBDRQQAF-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194 °C
• 沸点：
  659.9±65.0 °C(predicted)
• 密度：
  1.326±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基苯并噻唑 、 对二甲氨基苯甲醛 、 2-萘酚 反应 0.67h， 以93%的产率得到1-(benzo[d]thiazol-2-ylamino)(4-(dimethylamino)phenyl)-naphthalen-2-ol
  参考文献：
  名称：

  2-（二芳基烷基）氨基苯并噻唑衍生物的设计与绿色合成及其作为血管紧张素转化酶抑制剂和钙通道阻滞剂的双重活性

  摘要：

  基于商业合成的钙通道阻滞剂（CCBs）和血管紧张素转化酶（ACE）抑制剂，设计了一系列新型的2-（二芳基烷基）氨基苯并噻唑。根据作为血管紧张素转化酶（ACE）抑制剂的天然产物进一步修饰。为它们的合成开发了完全绿色的方案。由于它们最初是基于CCB设计的，因此对它们的ACE抑制性能进行了筛选，认为几乎所有化合物都是CCB。在42种化合物中，有2种先导分子被鉴定为ACE抑制剂，进一步筛选了CCB。如预期的那样，两个都被鉴定为对ACE抑制具有不同选择性的CCB。它们对ACE和CCB的选择性可用于治疗耐药性高血压。

  DOI：

  10.1016/j.ejmech.2014.06.035

文献信息

• Role of basicity and the catalytic activity of KOH loaded MgO and hydrotalcite as catalysts for the efficient synthesis of 1-[(2-benzothiazolylamino)arylmethyl]-2-naphthalenols
  作者：Pramod K. Sahu、Praveen K. Sahu、Dau D. Agarwal

  DOI：10.1039/c5ra11857c

  日期：——

  respectively. Hydrotalcite could be reused four times without a loss of the catalytic efficiency. Present catalytic system requires a short reaction time, is non toxic, easy to workup, has a good catalytic activity and gives a high efficiency.

  合成了新型的KOH负载的MgO和水滑石作为碱性催化剂，并通过XRD，SEM和碱度对其进行了表征。在醛，2-氨基苯并噻唑和2-萘酚的三组分反应中研究了KOH重量％，反应时间，碱度和催化剂负载量的影响。目前的研究表明了KOH负载和反应时间的影响。在70°C下获得的最佳转化率和产率分别为93％和88％。水滑石可以重复使用四次而不会降低催化效率。当前的催化体系需要短的反应时间，无毒，易于后处理，具有良好的催化活性并具有很高的效率。
• Role of surfactant and micelle-promoted mild, efficient, sustainable synthesis of 2-aminobenzothiazolomethyl naphthols and 5-(2-aminobenzothiazolomethyl)-6-hydroxyquinolines in water at room temperature
  作者：Pramod K. Sahu、Praveen K. Sahu、Dau D. Agarwal

  DOI：10.1039/c4ra03847a

  日期：——

  A new green protocol for the efficient surfactant catalyzed synthesis of 2-aminobenzothiazolomethyl naphthols and 5-(2-aminobenzothiazolomethyl)-6-hydroxyquinolines from substituted aromatic aldehydes, 2-aminobenzothiazole and 2-naphthol or 6-hydroxyquinoline at room temperature in water was developed for the first time. The influence of the sodium lauryl sulphate (SLS) micelles and their different concentrations on reactivity of 2-aminobenzothiazolomethyl naphthol was studied. It was found that best yield was obtained with 10 mol% catalyst loading with minimum time as compared to when other surfactants and catalysts were used. The best yield of product was achieved by using 10 mol% of SLS. This procedure resulted in a general and environmentally benign protocol and has the advantages of better reusability of the catalyst system, excellent yield, short reaction time and ease of work up.

  本研究首次开发了一种新的表面活性剂催化绿色合成方法，可在室温水中以取代的芳香醛、2-氨基苯并噻唑和 2-萘酚或 6-羟基喹啉为原料，高效合成 2-氨基苯并噻唑甲基萘酚和 5-(2-氨基苯并噻唑甲基)-6-羟基喹啉。研究了十二烷基硫酸钠（SLS）胶束及其不同浓度对 2-氨基苯并噻唑甲基萘酚反应性的影响。结果发现，与使用其他表面活性剂和催化剂时相比，使用 10 mol% 的催化剂时，能以最短的时间获得最佳产率。使用 10 mol% 的 SLS 可获得最佳产率。该方法是一种对环境无害的通用方案，具有催化剂系统可重复使用、产率高、反应时间短和易于操作等优点。
• Identification of Naphthol Derivatives as Novel Antifeedants and Insecticides. 1
  作者：Praveen Kumar Kalavagunta、Rajasekharreddy Pala、Usha Rani Pathipati、Narender Ravirala

  DOI：10.1021/jf501705u

  日期：2014.7.16

  A series of beta-naphthol-derived 2-aminobenzothiazolomethylnaphthol derivatives (4a-4q) were synthesized and purified in excellent yields (86-94%) using green protocols and screened for their antifeedant and toxic activities against tobacco caterpillar (Spodoptera litura) and castor semilooper (Achaea janata) using no-choice leaf disk and topical bioassay methods. Four of them, 4d, 4f, 4i, and 4j, were identified to be potent antifeedants with ED50 values of 16.4, 19.3, 7.0, and 5.2 mu g/cm(2) against S. litura and 13.9, 17.2, 10.2, and 7.7 mu g/cm(2) against A. janata, respectively, and the mortality rate is >95% for 4i and 4j in the case of S. litura and 4j in case of A. janata at a dosage of 0.2 mu g/insect. Compounds 4d, 4i, and 4m are moderately toxic to A. janata only. Overall, this study identified a novel class of synthetic compounds that do not belong to organochlorides, organophosphates, carbamates, or neonicotinoids as strong antifeedants as well as insecticides.