2-(2-aminopyridin-5-yl)benzothiazole | 178804-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(2-aminopyridin-5-yl)benzothiazole
• 英文别名: 5-(1,3-Benzothiazol-2-yl)pyridin-2-amine
• CAS: 178804-21-2
• 化学式: C₁₂H₉N₃S
• mdl: MFCD06660511
• 分子量: 227.29
• InChiKey: IOUXHHSEJFVUMU-UHFFFAOYSA-N

物化性质

• 沸点：
  444.9±55.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)
• 溶解度：
  17.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 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：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-aminopyridin-5-yl)benzothiazole 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以82%的产率得到2-(2-amino-3-bromopyridin-5-yl)benzothiazole
  参考文献：
  名称：

  Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo

  摘要：

  A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high-yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 mu M) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole much greater than benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'- iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER(+) (MCF-7 and BO) and ER(-) (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.

  DOI：

  10.1021/jm9600959
• 作为产物：
  描述：

  6-氨基烟酸 、 2-氨基苯硫醇 在 PPA 作用下， 反应 4.0h， 以59%的产率得到2-(2-aminopyridin-5-yl)benzothiazole
  参考文献：
  名称：

  Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo

  摘要：

  A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high-yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 mu M) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole much greater than benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'- iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER(+) (MCF-7 and BO) and ER(-) (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.

  DOI：

  10.1021/jm9600959

文献信息

• Method for optical measurement of multi-stranded nucleic acid
  申请人：Nakamura Kouki

  公开号：US20050112770A1

  公开（公告）日：2005-05-26

  A method for optical measurement of a multi-stranded nucleic acid which comprises the step of bringing a compound into contact with a multi-stranded nucleic acid wherein said compound is capable of interacting with the multi-stranded nucleic acid, wherein the compound has the following properties: (a) the compound can exist in a substantially colorless and non-fluorescent state under at least one condition in an aqueous solution in the absence of the multi-stranded nucleic acid, and (b) when the multi-stranded nucleic acid is allowed to exist in the condition defined in the above (a), the compound changes to a substantially colored state based on an interaction with the multi-stranded nucleic acid and substantially expresses fluorescent property based on said interaction.

  一种用于多股核酸的光学测量方法，包括以下步骤：将一种化合物与多股核酸接触，所述化合物能够与多股核酸相互作用，且该化合物具有以下性质：(a) 在无多股核酸的情况下，该化合物能够在水溶液中在至少一种条件下处于基本无色和非荧光状态，(b) 当多股核酸存在于上述(a)定义的状态下时，该化合物会因与多股核酸的相互作用而转变为基本上有色的状态，并基于该相互作用而表现出基本上荧光的性质。
• METHOD FOR OPTICAL MEASUREMENT OF MULTI-STRANDED NUCLEIC ACID
  申请人：NAKAMURA Kouki

  公开号：US20080124732A1

  公开（公告）日：2008-05-29

  A method for optical measurement of a multi-stranded nucleic acid which comprises the step of bringing a compound into contact with a multi-stranded nucleic acid wherein said compound is capable of interacting with the multi-stranded nucleic acid, wherein the compound has the following properties: (a) the compound can exist in a substantially colorless and non-fluorescent state under at least one condition in an aqueous solution in the absence of the multi-stranded nucleic acid, and (b) when the multi-stranded nucleic acid is allowed to exist in the condition defined in the above (a), the compound changes to a substantially colored state based on an interaction with the multi-stranded nucleic acid and substantially expresses fluorescent property based on said interaction.

  一种用于光学测量多股核酸的方法，包括以下步骤：将一种化合物与多股核酸接触，其中该化合物能够与多股核酸相互作用，该化合物具有以下特性：（a）在无多股核酸存在的情况下，在水溶液中至少有一个条件下，该化合物可以存在于基本无色且不发荧光的状态；（b）当多股核酸被允许在上述（a）所定义的条件下存在时，该化合物会因与多股核酸的相互作用而转变为基本上带色的状态，并基于该相互作用表现出基本上发荧光的特性。
• Discovery, synthesis and biological evaluation of a series of N-(phenylcarbamothioyl)-2-napthamides as inhibitors of Claudin-1
  作者：Viktoriya Mashinson、Thomas M. Webster、Anish K. Vadukoot、Kirsten T. Tolentino、Princess Simeon、Iram Fatima、Punita Dhawan、Corey R. Hopkins

  DOI：10.1016/j.bmc.2023.117416

  日期：2023.9

  claudin-1 may have therapeutic potential for the treatment of CRC. Previously, we have identified a small molecule that inhibits claudin-1 dependent CRC progression. Reported herein are our lead optimization efforts around this scaffold to identify the key SAR components and the discovery of a key new compound that exhibits enhanced potency in SW620 cells.

  尽管诊断技术取得了进步，结直肠癌（CRC）仍然是全世界癌症相关死亡的主要原因。主要原因是许多新诊断的CRC患者会出现其他器官的转移。因此，新疗法的开发至关重要。 Claudin-1 蛋白是上皮细胞（包括结肠内壁细胞）紧密连接的组成部分。它在紧密连接的形成和维持中起着关键作用，这对于调节细胞之间的分子通道至关重要。在结直肠癌中，claudin-1 通常过度表达，导致细胞粘附增加，从而促进疾病的发生和进展。研究表明，高水平的claudin-1与结直肠癌患者的不良预后相关，靶向claudin-1可能具有治疗结直肠癌的潜力。此前，我们已经鉴定出一种抑制claudin-1依赖性CRC进展的小分子。本文报道了我们围绕该支架的主要优化工作，以确定关键的 SAR 成分，并发现了一种在 SW620 细胞中表现出增强效力的关键新化合物。
• Method for optical measurement of multi-stranded nucleic acid using cyanine dyes
  申请人：FUJIFILM Corporation

  公开号：EP1362894B1

  公开（公告）日：2007-12-19