4-(1,3-苯并噻唑-2-甲基)苯胺 | 37859-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 4-(1,3-苯并噻唑-2-甲基)苯胺
• 英文名称: 4-(benzo[d]thiazol-2-ylmethyl)aniline
• 英文别名: 4-(1,3-Benzothiazol-2-ylmethyl)aniline
• CAS: 37859-28-2
• 化学式: C₁₄H₁₂N₂S
• mdl: MFCD03773367
• 分子量: 240.329
• InChiKey: GUUPKXREMJGASF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934200090

反应信息

• 作为反应物：
  描述：

  对甲基苯乙酸 、 4-(1,3-苯并噻唑-2-甲基)苯胺 在 氯化亚砜 、 碳酸氢钠 作用下， 以 苯 、 乙醚 、 水 为溶剂， 反应 3.0h， 以48%的产率得到2-[4-(4-methylphenylacetamido)benzyl]benzothiazole
  参考文献：
  名称：

  Synthesis and In vitro Antimicrobial Activity of Novel 2-(4-(Substituted-carboxamido)benzyl / phenyl)benzothiazoles

  摘要：

  A new series of 2-[4-(4-substitutedbenzamido / phenylacetamido / phenylpropionamido) benzyl / phenyl]benzothiazole derivatives (6a-6w) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli with their drug-resistant isolates and a yeast Candida albicans. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 200 and 6.25 mu g/ml. Compounds 6e and 6j exhibited the greatest activity with MIC values of 6.25 mu g/ml against Pseudomonas aeruginosa, and Staphylococcus aureus isolate, respectively.

  DOI：

  10.5562/cca2064
• 作为产物：
  描述：

  对氨基苯乙酸 、 2-氨基苯硫醇 以 neat (no solvent) 为溶剂， 反应 14.0h， 生成 4-(1,3-苯并噻唑-2-甲基)苯胺
  参考文献：
  名称：

  合成吡咯烷酮合成苯并噻唑啉酮光致变色剂在位置3中

  摘要：

  螺环吡喃酮的合成光铬在某些情况下替代了三环蒙特卡罗环法分类限量版，并在多氯联苯和多氯联苯上起到了保护作用。sériebenzothiazolinique合成和临时化的构成。新的基础知识注入光变色的参差不齐的影响（变色热敏化，敏感光谱）。综合音乐谱系。

  DOI：

  10.1002/hlca.19720550538

文献信息

• Multifunctional iron-chelators with protective roles against neurodegenerative diseases
  作者：Andreia Nunes、Sérgio M. Marques、Catarina Quintanova、Diana F. Silva、Sandra M. Cardoso、Sílvia Chaves、M. Amélia Santos

  DOI：10.1039/c3dt50406a

  日期：——

  anti-acetylcholinesterase activity. Therefore, 3-hydroxy-4-pyridinone (3,4-HP) and benzothiazole molecular moieties were selected as starting frameworks due to their well known affinity for iron and Aβ peptides, respectively. The linkers between these two main functional groups were selected on the basis of virtual screening, so that the final molecule could further inhibit the acetylcholinesterase, responsible for the

  阿尔茨海默氏病（AD）的多因素性质以及缺乏疾病改良药物，使得开发新的多功能药物成为一种有吸引力的治疗策略。考虑到AD患者大脑的特点，例如乙酰胆碱水平低，蛋白质错误折叠和相关的β-淀粉样蛋白（Aβ）聚集，氧化应激和金属动态异常，我们开发了一系列化合物，这些化合物合并了三种不同的方法：金属减毒，抗Aβ聚集和抗乙酰胆碱酯酶活性。所以，3-羟基-4-吡啶酮 （3,4-HP）和 苯并噻唑由于分子部分分别对铁和Aβ肽的熟知的亲和力，因此选择分子部分作为起始框架。在虚拟筛选的基础上选择了这两个主要功能基团之间的接头，以便最终分子可以进一步抑制乙酰胆碱酯酶，这是造成胆碱能丧失的原因。我们在本文中描述了新杂化化合物的设计和合成，然后评估了溶液的性质，即铁螯合和抗氧化能力。对这些化合物具有抑制AChE的能力以及自身和锌介导的Aβ1–42聚集的能力进行了生物测定。最后，我们评估了它们对Aβ42应激神经元细胞活力的影响。
• Neurologically active compounds and compounds with multiple activities
  申请人：——

  公开号：US20040092536A1

  公开（公告）日：2004-05-13

  This invention provides pharmacologically active compounds having neurological and other bio-active capability. These active compounds comprise the derivatives of guanidino, aminoguanidino, 2-imadazolino, 2-hydrazinoimidazolino or 2-guanidinobenzimidazolino groups.

  本发明提供具有神经和其他生物活性能力的药理活性化合物。这些活性化合物包括鸟氨酸衍生物、氨基鸟氨酸衍生物、2-咪唑啉衍生物、2-肼基咪唑啉衍生物或2-鸟氨酰基苯并咪唑啉衍生物。
• NEUROLOGICALLY ACTIVE COMPOUNDS AND COMPOUNDS WITH MULTIPLE ACTIVITIES
  申请人：Naftchi Eric N.

  公开号：US20070082918A1

  公开（公告）日：2007-04-12

  Pharmacologically active compounds suitable for treating a mammal so as to affect neurological function, the compounds comprising at least two neurologically active groups, one group providing alpha-adrenergic agonist activity, and the second group providing agonist activity selected from the group consisting of beta-adrenergic agonist activity, serotinergic agonist activity, dopaminergic agonist activity, and GABA-ergic agonist activity. Each of the compounds being lipophilic, capable of crossing the blood/central nervous system barrier and effective as the primary therapeutic agent, in a dosage amount and at a dosage rate sufficient to provide the desired effect. Therapeutic compositions comprising the compound are provided.

  具有药理活性的化合物，适用于治疗哺乳动物以影响神经功能，该化合物包括至少两个神经活性基团，其中一个基团提供α-肾上腺素能激动剂活性，第二个基团提供从以下组中选择的激动剂活性：β-肾上腺素能激动剂活性、血清素能激动剂活性、多巴胺能激动剂活性和GABA-能激动剂活性。每种化合物都是亲脂性的，能够穿过血液/中枢神经系统屏障，并且在剂量和剂量速率足以提供所需效果的情况下作为主要治疗剂有效。提供了包含该化合物的治疗组合物。
• 一种2H-苯并噻唑C2苄基化衍生物的合成方法
  申请人：浙江工业大学

  公开号：CN114163399B

  公开（公告）日：2023-02-28

  本发明公开了一种2H‑苯并噻唑C2苄基化衍生物的合成方法，具体制备方法为将2H‑苯并噻唑与取代甲基苯混合，加入氧化剂Selectfluor、添加剂四丁基碘化铵，进行加热搅拌反应，TLC监测至反应结束后，反应液分离纯化制得2H‑苯并噻唑C2苄基化衍生物。本发明具有反应温度较低、反应条件温和、反应收率较高以及原子经济性好等优点。
• Design, synthesis and neuroprotective evaluation of novel tacrine–benzothiazole hybrids as multi-targeted compounds against Alzheimer’s disease
  作者：Rangappa S. Keri、Catarina Quintanova、Sérgio M. Marques、A. Raquel Esteves、Sandra M. Cardoso、M. Amélia Santos

  DOI：10.1016/j.bmc.2013.05.028

  日期：2013.8

  Alzheimer's disease (AD) is a multifactorial disorder with several target proteins contributing to its etiology. In search for multifunctional anti-AD drug candidates, taking into account that the acetylcholinesterase (AChE) and beta-amyloid (A beta) aggregation are particularly important targets for inhibition, the tacrine and benzothiazole (BTA) moieties were conjugated with suitable linkers in a novel series of hybrids. The designed compounds (7a-7e) were synthesized and in vitro as well as in ex vivo evaluated for their capacity for the inhibition of acetylcholinesterase (AChE) and A beta self-induced aggregation, and also for the protection of neuronal cells death (SHSY-5Y cells, AD and MCI cybrids). All the tacrine-BTA hybrids displayed high in vitro activities, namely with IC50 values in the low micromolar to sub-micromolar concentration range towards the inhibition of AChE, and high percentages of inhibition of the self-induced A beta aggregation. Among them, compound 7a, with the shortest linker, presented the best inhibitory activity of AChE (IC50 = 0.34 mu M), while the highest activity as anti-A beta(42) self-aggregation, was evidenced for compound 7b (61.3%, at 50 mu M. The docking studies demonstrated that all compounds are able to interact with both catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. Our results show that compounds 7d and 7e improved cell viability in cells treated with A beta(42) peptide. Overall, these multi-targeted hybrid compounds appear as promising lead compounds for the treatment of Alzheimer's disease. (C) 2013 Elsevier Ltd. All rights reserved.