2-amino-5,6,7-trimethoxybenzothiazole | 127346-17-2

• 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-amino-5,6,7-trimethoxybenzothiazole
• 英文别名: 5,6,7-trimethoxy-1,3-benzothiazol-2-amine
• CAS: 127346-17-2
• 化学式: C₁₀H₁₂N₂O₃S
• mdl: MFCD11189735
• 分子量: 240.283
• InChiKey: QXLGLDSJSSVMTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-5,6,7-trimethoxybenzothiazole 在 potassium hydroxide 作用下， 以 水 、 乙二醇 为溶剂， 反应 24.0h， 以77%的产率得到bis(3,4,5-trimethoxyanilin-2-yl)disulfide
  参考文献：
  名称：

  5-（5,6-二甲氧基苯并噻唑-2-基）-2'-脱氧尿苷（dbtU）和含有dbtU的寡脱氧核糖核苷酸的荧光性质

  摘要：

  描述了11个含d bt U的5–（苯并噻唑-2-基）-2 -'-脱氧尿苷衍生物和寡脱氧核糖核苷酸（ODN）的光物理性质。比较了包含5'-X bt U-3'和5'- bt UY-3'的16种组合的ODN的荧光特性，发现d bt U是一种非常有前途的新荧光类似物，但对Dbt U的敏感性较低。它在DNA中的微环境。

  DOI：

  10.1002/ejoc.201100818
• 作为产物：
  描述：

  硫氰酸铵 、 3,4,5-三甲氧基苯胺 在 N,N,N-trimethylbenzenemethanaminium dichloroiodate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 以89%的产率得到2-amino-5,6,7-trimethoxybenzothiazole
  参考文献：
  名称：

  在 DMSO:H2O 中使用苄基三甲基二氯碘酸铵和硫氰酸铵从取代苯胺高效一锅法合成 2-氨基苯并噻唑

  摘要：

  在 DMSO:H 2 O (9:1) 中，在 70 °C 下用苄基三甲基二氯碘酸铵（1.2 当量）和硫氰酸铵（1.0 当量）处理各种取代苯胺，得到相应的 2-氨基苯并噻唑，分离产率高（75-97 %；所有底物的平均产率 = 90%）。该反应适用于 2(4)-单-、2,4-二-或 3,4,5-三-取代的苯胺，以及范围广泛的两种给电子基团（MeO、H2O、CF 3 O、 Me）和吸电子基团（NO 2、CN、CO 2 Et、CO 2 H、Cl、F）耐受性良好。这种方法为其他方法提供了一种有用的替代方法，这些方法要么效率较低（需要 3-7 倍当量的试剂），要么使用剧毒和腐蚀性液体溴2作为氧化剂。

  DOI：

  10.1016/j.tetlet.2021.153388

文献信息

• Cu-Catalyzed Direct C–P Bond Formation through Dehydrogenative Cross-Coupling Reactions between Azoles and Dialkyl Phosphites
  作者：Soumyadip Hore、Abhijeet Srivastava、Ravi P. Singh

  DOI：10.1021/acs.joc.9b00670

  日期：2019.6.7

  cross-coupling of azoles [C(sp2)–H] with dialkyl phosphites [P(O)–H] to access 2-phosphonated azoles using Cu(I)/Cu(II) as catalyst and K2S2O8/di-tert-butylperoxide as oxidant has been achieved. A remarkable advantage over reported procedures includes that oxazoles, imidazoles, benz(ox/othi/imid)azoles, and indole are found to react under optimized reaction conditions to provide corresponding adducts in

  吡咯[C（sp 2）–H]与亚磷酸二烷基酯[P（O）–H]的直接脱氢交叉偶联，以Cu（I）/ Cu（II）为催化剂和K 2 S来获得2-膦酸化的吡咯已获得2 O 8 /二叔丁基过氧化物作为氧化剂。与报道的方法相比，一个显着的优势包括发现恶唑，咪唑，苯并（ox / othi /咪唑）和吲哚在优化的反应条件下反应，可以高产率提供相应的加合物。通过氘动力学同位素效应研究获得了交叉耦合的机理见解。
• Imidazo[2,1-B]benzothiazole compounds and antiulcer compositions
  申请人：Nikken Chemicals Co., Ltd.

  公开号：US04968708A1

  公开（公告）日：1990-11-06

  The present invention relates to novel imidazo-[2,1-b]benzothiazole compounds represented by formula (I) and pharmacological acceptable salts thereof: ##STR1## wherein R.sub.1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms; R.sub.2 represents a ##STR2## group (wherein X and Y, which may be the same or different, each represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group), a --CH.sub.2 --O--Z group (wherein Z represents a lower alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted benzyl group) or a --CH.sub.2 --O--CO--W group (wherein W represents an alkyl group having 1 to 8 carbon atoms, an alkylamino group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group or a thienyl group); and R.sub.3 ; R.sub.4 and R.sub.5, which may be the same or different, each represents a hydrogen atom, a halogen atom or a lower alkoxy group having 1 to 4 carbon atoms, and antiulcer compositions comprising as the efective ingredient the compounds.

  本发明涉及由式(I)表示的新型咪唑-[2,1-b]苯并噻唑化合物及其药学上可接受的盐：##STR1##其中R.sub.1代表氢原子或具有1至4个碳原子的较低烷基基团；R.sub.2代表##STR2##基团（其中X和Y，可以相同也可以不同，每个代表氢原子，具有1至4个碳原子的较低烷基基团或取代或未取代的苯基团），一个--CH.sub.2--O--Z基团（其中Z代表具有1至4个碳原子的较低烷基基团或取代或未取代的苄基团）或一个--CH.sub.2--O--CO--W基团（其中W代表具有1至8个碳原子的烷基基团，具有1至8个碳原子的烷基氨基基团，取代或未取代的苯基团或噻吩基团）；以及R.sub.3；R.sub.4和R.sub.5，可以相同也可以不同，每个代表氢原子，卤原子或具有1至4个碳原子的较低烷氧基团，以及作为有效成分的抗溃疡组合物。
• Small-compound enhancers for functional O-mannosylation of alpha-dystroglycan, and uses thereof
  申请人：Wu Xiaohua

  公开号：US10221168B1

  公开（公告）日：2019-03-05

  The present invention provides compounds that can enhance functional O-mannosylation of proteins including alpha-dystroglycan. Also provided are methods of preparation of the compounds defined by the formula I. Also provided are the methods of using the compounds or the pharmaceutical acceptable salts or prodrugs thereof in treating and preventing subjects suffering from the diseases including muscular dystrophies and cancers.

  本发明提供了一种可以增强蛋白质的O-甘露糖基化功能，包括α-骨骼肌糖蛋白的化合物。还提供了一种按照式I定义的化合物的制备方法。同时提供了使用这些化合物或其药用可接受的盐或前药来治疗和预防患有包括肌肉萎缩症和癌症在内的疾病的方法。
• Imidazo[2,1-b]benzothiazole compounds and antiulcer compositions containing the same
  申请人：NIKKEN CHEMICALS CO., LTD.

  公开号：EP0347880A2

  公开（公告）日：1989-12-27

  The present invention relates to novel imidazo­[2,1-b]benzothiazole compounds represented by formula (I) and pharmacological acceptable salts thereof: wherein R₁ represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms; R₂ represents a group (wherein X and Y, which may be the same or different, each represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted phenyl group), a -CH₂-O-Z group (wherein Z represents a lower alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted benzyl group) or a -CH₂-O-CO-W group (wherein W represents an alkyl group having 1 to 8 carbon atoms, an alkylamino group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group or a thienyl group); and R₃, R₄ and R₅, which may be the same or different, each represents a hydrogen atom, a halogen atom or a lower alkoxy group having 1 to 4 carbon atoms and antiulcer compositions comprising as the effective ingredient the compounds.

  本发明涉及式(I)代表的新型咪唑并[2,1-b]苯并噻唑化合物及其药理学上可接受的盐： 其中 R₁ 代表氢原子或具有 1 至 4 个碳原子的低级烷基； R₂ 代表 基团(其中 X 和 Y 可以相同或不同，各自代表氢原子、具有 1 至 4 个碳原子的低级烷基或取代或未取代的苯基)、-CH₂-O-Z-基团（其中 Z 代表具有 1 至 4 个碳原子的低级烷基或取代或未取代的苄基）或-CH₂-O-CO-W-基团（其中 W 代表具有 1 至 8 个碳原子的烷基、具有 1 至 8 个碳原子的烷基氨基、取代或未取代的苯基或噻吩基）；和 R₃、R₄ 和 R₅，它们可以相同或不同，各自代表氢原子、卤素原子或具有 1 至 4 个碳原子的低级烷氧基，以及包含这些化合物作为有效成分的抗溃疡组合物。
• Small molecules enhance functional O-mannosylation of Alpha-dystroglycan
  作者：Fengping Lv、Zhi-fang Li、Wenhao Hu、Xiaohua Wu

  DOI：10.1016/j.bmc.2015.11.011

  日期：2015.12

  Alpha-dystroglycan (alpha-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of alpha-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of alpha-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of alpha-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of alpha-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of alpha-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of alpha-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. (c) 2015 Elsevier Ltd. All rights reserved.