6-nitro-N-(tetrahydro-2H-pyran-4-yl)benzo[d]thiazol-2-amine | 659743-22-3

• 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: 6-nitro-N-(tetrahydro-2H-pyran-4-yl)benzo[d]thiazol-2-amine
• 英文别名: (6-nitrobenzothiazol-2-yl)-(tetrahydropyran-4-yl)-amine；6-nitro-N-(oxan-4-yl)-1,3-benzothiazol-2-amine
• CAS: 659743-22-3
• 化学式: C₁₂H₁₃N₃O₃S
• 分子量: 279.32
• InChiKey: ZASHSWAVDPFVTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  465.5±55.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-nitro-N-(tetrahydro-2H-pyran-4-yl)benzo[d]thiazol-2-amine 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-[2-(tetrahydropyran-4-ylamino)benzothiazol-6-yl]thiophene-2-carboxamidine
  参考文献：
  名称：

  Novel 2-aminobenzothiazoles as selective neuronal nitric oxide synthase inhibitors

  摘要：

  A series of substituted 2-aminobenzothiazole compounds have been synthesized and evaluated as nitric oxide synthase (NOS) inhibitors. Compound 14 shows activity in the nM range and is selective for the human neuronal NOS isoform. We have also evaluated the compounds against the rat NOS isoforms. For some of the compounds, there are significant differences in NOS inhibitory activities between the human and rat enzymes. For example, compound 10b has nM activity against the rat nNOS while low mu M activity against the human nNOS. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.011
• 作为产物：
  描述：

  (6-硝基苯并噻唑-2-基)-肼 在 氯化亚砜 作用下， 生成 6-nitro-N-(tetrahydro-2H-pyran-4-yl)benzo[d]thiazol-2-amine
  参考文献：
  名称：

  Novel 2-aminobenzothiazoles as selective neuronal nitric oxide synthase inhibitors

  摘要：

  A series of substituted 2-aminobenzothiazole compounds have been synthesized and evaluated as nitric oxide synthase (NOS) inhibitors. Compound 14 shows activity in the nM range and is selective for the human neuronal NOS isoform. We have also evaluated the compounds against the rat NOS isoforms. For some of the compounds, there are significant differences in NOS inhibitory activities between the human and rat enzymes. For example, compound 10b has nM activity against the rat nNOS while low mu M activity against the human nNOS. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.011

文献信息

• Rational Design, synthesis and biological evaluation of novel triazole derivatives as potent and selective PRMT5 inhibitors with antitumor activity
  作者：Kongkai Zhu、Jingwei Shao、Hongrui Tao、Xue Yan、Cheng Luo、Hua Zhang、Wenhu Duan

  DOI：10.1007/s10822-019-00214-y

  日期：2019.8

  tumorigenesis, development and poor clinical outcomes of human cancers. Two PRMT5 small molecule inhibitors (GSK3326595 and JNJ-64619178) have been put forward into clinical trials. Here, we describe the design, synthesis and biological evaluation of a series of novel, potent and selective PRMT5 inhibitors with antiproliferative activity against Z-138 mantle cell lymphoma cell line. Among them, compound

  蛋白质精氨酸甲基转移酶5（PRMT5）负责精氨酸的单甲基化和对称二甲基化，其表达水平和甲基转移活性已被证明与人类癌症的发生，发展和不良的临床预后密切相关。两种PRMT5小分子抑制剂（GSK3326595和JNJ-64619178）已被提出用于临床试验。在这里，我们描述了一系列新颖，有效和选择性的PRMT5抑制剂的设计，合成和生物学评估，这些抑制剂对Z-138套细胞淋巴瘤细胞系具有抗增殖活性。其中，化合物C_4的酶和细胞水平IC50值分别为0.72和2.6μM，显示出最高的效力，并且对PRMT5的选择性比其他几种同工酶（PRMT1，PRMT4和PRMT6）。此外，C_4表现出明显的细胞凋亡作用，同时降低了SmD3蛋白的细胞对称精氨酸二甲基化水平。该化合物类别的效力，体积小和可合成的可及性为药物化学家提供了有前途的命中支架，以进一步探索该系列的PRMT5抑制剂。
• 含四氢异喹啉的磺胺类和苯并噻唑类化合物的制备及应用
  申请人：济南大学

  公开号：CN110950801A

  公开（公告）日：2020-04-03

  本发明公开了一种图1所示的含有四氢异喹啉的磺胺类化合物和图2所示的含有四氢异喹啉的苯并噻唑类化合物以及它们作为新型蛋白精氨酸甲基转移酶5抑制剂的应用。
• Amino benzothiazole compounds with NOS inhibitory activity
  申请人：Ramnauth Jailall

  公开号：US20050209291A1

  公开（公告）日：2005-09-22

  The present invention provides novel amino benzothiazole compounds, compositions comprising these compounds and methods of using these compounds as neuroprotectants. In particular, the compounds described in the present invention are useful for treating stroke and neuropathic pain.

  本发明提供了新型氨基苯并噻唑化合物，包括这些化合物的组合物以及使用这些化合物作为神经保护剂的方法。特别是，本发明所描述的化合物对于治疗中风和神经病性疼痛非常有用。
• AMINO BENZOTHIAZOLE COMPOUNDS WITH NOS INHIBITORY ACTIVITY
  申请人：Neuraxon Inc.

  公开号：EP1539724B1

  公开（公告）日：2007-10-10
• US7141595B2
  申请人：——

  公开号：US7141595B2

  公开（公告）日：2006-11-28