N~6~,N~6~-二甲基-1,3-苯并噻唑-2,6-二胺 | 64334-41-4

• 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: N~6~,N~6~-二甲基-1,3-苯并噻唑-2,6-二胺
• 英文名称: N⁶,N⁶-dimethylbenzo[d]thiazole-2,6-diamine
• 英文别名: N6,N6-Dimethylbenzo[d]thiazole-2,6-diamine；6-N,6-N-dimethyl-1,3-benzothiazole-2,6-diamine
• CAS: 64334-41-4
• 化学式: C₉H₁₁N₃S
• 分子量: 193.272
• InChiKey: DCUFLOLNQPJBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  N~6~,N~6~-二甲基-1,3-苯并噻唑-2,6-二胺 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 9.0h， 生成 3-[6-(Dimethylamino)-1,3-benzothiazol-2-yl]-6-phenyl-1,3-oxazinane-2-thione
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activity of 3-(6-Substituted-benzothiazol-2-yl)-6-phenyl-[1, 3]-xazinane-2-thiones

  摘要：

  A new series of 3-(6-substituted-benzothiazol-2-yl)-6-phenyl-[1,3]-oxazinane-2-thiones (4 a-j) has been synthesised using an appropriate synthetic route (Scheme 1) and characterised by elemental analyses and spectral (IR, H-1 NMR, C-13 NMR, and El MS) data. The anticonvulsant activity of all the title compounds (4 a-j) was evaluated against Maximal Electroshock (MES) induced seizures and furthermore the most potent compounds were evaluated against subcutaneous pentylene-in mice. The neurotoxicity was assessed tetrazole (sc PTZ) induced seizures model, using the rotorod procedure. All the test compounds were administered intraperitoneally at various dose levels ranging from 30-200 mg/kg body wt and the median effective dose (ED50), median toxic dose (TD50), and protection index (PI) values were determined (Table 2). Among the compounds tested, the 3-(6-dimethylaminobenzothiazol-2-yl)-6-phenyl-[1,3]-oxazinane-2-thiones (4j) was found to be the most potent (ED50: 9.85 and 14.8 in MES model and 12 and 17 in scPTZ model at t = 0.5 h and 4 h, respectively, and TD50 42.8 and 44 at t = 0.5 h and 4 h, respectively, which has been found to be significant at p < 0.01 with respect to reference standard phenytoin) with protection index (PI) 4.85.

  DOI：

  10.1002/1521-4184(200211)335:8<381::aid-ardp381>3.0.co;2-s
• 作为产物：
  描述：

  N²,N²-di(Boc)-N⁶,N⁶-dimethylbenzo[d]thiazole-2,6-diamine 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以95 %的产率得到N~6~,N~6~-二甲基-1,3-苯并噻唑-2,6-二胺
  参考文献：
  名称：

  Development of submicromolar 17β-HSD10 inhibitors and their in vitro and in vivo evaluation

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115593

文献信息

• Discovery of benzothiazole amides as potent antimycobacterial agents
  作者：James Graham、Christina E. Wong、Joshua Day、Elizabeth McFaddin、Urs Ochsner、Teresa Hoang、Casey L. Young、Wendy Ribble、Mary A. DeGroote、Thale Jarvis、Xicheng Sun

  DOI：10.1016/j.bmcl.2018.08.026

  日期：2018.10

  against nontuberculous mycobacteria and Mycobacterium tuberculosis, numerous hits were identified with moderate activity. Extensive medicinal chemistry optimization has led to a series of potent benzothiazole amide antimycobacterial agents. Replacement of the adamantyl group with cyclohexyl derivatives and further development of this series resulted in an advanced lead compound, CRS400393, which demonstrated

  通过对市售非结核分枝杆菌和结核分枝杆菌文库的高通量筛选，鉴定出许多具有中等活性的命中。广泛的药物化学优化产生了一系列有效的苯并噻唑酰胺抗分枝杆菌药物。用环己基衍生物取代金刚烷基，并进一步开发该系列，产生了先进的先导化合物CRS400393 ，它表现出优异的效力和分枝杆菌特异性的活性谱。针对脓肿分枝杆菌和其他快速生长 NTM 的 MIC 值范围为 0.03 至 0.12 μg/mL，针对鸟分枝杆菌复合体的 MIC 值范围为 1-2 μg/mL。初步作用机制研究表明这些药物可能以 MmpL3（一种分枝杆菌分枝菌酸转运蛋白）为目标。该系列已在脓肿分枝杆菌感染的概念验证小鼠模型中证明了体内功效。
• Heller, Journal fur praktische Chemie (Leipzig 1954), 1924, vol. <2> 108, p. 267
  作者：Heller

  DOI：——

  日期：——
• Kiprianov,A.I.; Mikhailenko,F.A., Journal of general chemistry of the USSR, 1963, vol. 33, p. 1381 - 1385
  作者：Kiprianov,A.I.、Mikhailenko,F.A.

  DOI：——

  日期：——
• Synthesis and Anticonvulsant Activity of 3-(6-Substituted-benzothiazol-2-yl)-6-phenyl-[1, 3]-xazinane-2-thiones
  作者：Rajendra S. Chopade、Rajesh H. Bahekar、Pramod B. Khedekar、Kishore P. Bhusari、Akkinpalli Raghu Ram Rao

  DOI：10.1002/1521-4184(200211)335:8<381::aid-ardp381>3.0.co;2-s

  日期：2002.11

  A new series of 3-(6-substituted-benzothiazol-2-yl)-6-phenyl-[1,3]-oxazinane-2-thiones (4 a-j) has been synthesised using an appropriate synthetic route (Scheme 1) and characterised by elemental analyses and spectral (IR, H-1 NMR, C-13 NMR, and El MS) data. The anticonvulsant activity of all the title compounds (4 a-j) was evaluated against Maximal Electroshock (MES) induced seizures and furthermore the most potent compounds were evaluated against subcutaneous pentylene-in mice. The neurotoxicity was assessed tetrazole (sc PTZ) induced seizures model, using the rotorod procedure. All the test compounds were administered intraperitoneally at various dose levels ranging from 30-200 mg/kg body wt and the median effective dose (ED50), median toxic dose (TD50), and protection index (PI) values were determined (Table 2). Among the compounds tested, the 3-(6-dimethylaminobenzothiazol-2-yl)-6-phenyl-[1,3]-oxazinane-2-thiones (4j) was found to be the most potent (ED50: 9.85 and 14.8 in MES model and 12 and 17 in scPTZ model at t = 0.5 h and 4 h, respectively, and TD50 42.8 and 44 at t = 0.5 h and 4 h, respectively, which has been found to be significant at p < 0.01 with respect to reference standard phenytoin) with protection index (PI) 4.85.
• Development of submicromolar 17β-HSD10 inhibitors and their in vitro and in vivo evaluation
  作者：Ondrej Benek、Michaela Vaskova、Marketa Miskerikova、Monika Schmidt、Rudolf Andrys、Aneta Rotterova、Adam Skarka、Jana Hatlapatkova、Jana Zdarova Karasova、Matej Medvecky、Lukas Hroch、Lucie Vinklarova、Zdenek Fisar、Jana Hroudova、Jiri Handl、Jan Capek、Tomas Rousar、Tereza Kobrlova、Rafael Dolezal、Ondrej Soukup、Laura Aitken、Frank Gunn-Moore、Kamil Musilek

  DOI：10.1016/j.ejmech.2023.115593

  日期：2023.10