3-(吗啉-4-基甲基)-1,3-苯并噻唑-2-硫酮 | 27410-41-9

• 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: 3-(吗啉-4-基甲基)-1,3-苯并噻唑-2-硫酮
• 英文名称: 3-(morpholin-4-ylmethyl)-2H,3H-1,3-benzothiazole-2-thione
• 英文别名: 3-(4-morpholinomethyl)-1,3-benzothiazole-2(3H)-thione；1-(morpholin-1-ylmethyl)benzothiazole-2-thione；3-morpholinomethyl-2-thiono-benzothiazole；3-morpholin-4-ylmethyl-3H-benzothiazole-2-thione；3-morpholinomethyl-3H-benzothiazole-2-thione；3-Morpholinomethyl-3H-benzothiazol-2-thion；2-Benzothiazolinethione, 3-(morpholinomethyl)-；3-(morpholin-4-ylmethyl)-1,3-benzothiazole-2-thione
• CAS: 27410-41-9
• 化学式: C₁₂H₁₄N₂OS₂
• mdl: MFCD00086522
• 分子量: 266.388
• InChiKey: YGYXYFFFRWOVAE-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C
• 沸点：
  412.8±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  73.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-巯基苯并噻唑 以 乙醇 、 水 、 丙酮 为溶剂， 生成 3-(吗啉-4-基甲基)-1,3-苯并噻唑-2-硫酮
  参考文献：
  名称：

  Stavrovskaya,V.I.; Kolosova,M.O., Journal of general chemistry of the USSR, 1960, vol. 30, p. 711 - 715

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of aminomethyl and alkoxymethyl derivatives as carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitors
  作者：İlhami Gulçin、Malahat Abbasova、Parham Taslimi、Zübeyir Huyut、Leyla Safarova、Afsun Sujayev、Vagif Farzaliyev、Şükrü Beydemir、Saleh H. Alwasel、Claudiu T. Supuran

  DOI：10.1080/14756366.2017.1368019

  日期：2017.1.1

  synthesized by a reaction with hemiformals, which are prepared by the reaction of alcohols and formaldehyde. In this study, the inhibitory effects of these molecules were investigated against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) enzymes and carbonic anhydrase I, and II isoenzymes (hCA I and II). Both hCA isoenzymes were significantly inhibited by the recently synthesized molecules

  含氮和硫原子的化合物可广泛用于工业，医学，生物技术和化学技术等各个领域。因此，开发了巯基苯并噻唑，巯基苯并恶唑和2-氨基噻唑的氨基甲基化和烷氧基甲基化反应。此外，巯基苯并恶唑和2-氨基噻唑的烷氧基甲基衍生物是通过与半缩醛反应合成的，半缩醛是通过醇与甲醛反应制得的。在这项研究中，研究了这些分子对乙酰胆碱酯酶（AChE），丁酰胆碱酯酶（BChE）酶和碳酸酐酶I和II同工酶（hCA I和II）的抑制作用。两种hCA同工酶均被最近合成的分子显着抑制，hCA I的Ki值在58-157 nM之间，hCA II为81-215 nM。此外，这些分子的BChE和AChE的Ki参数分别在23-88和18-78 nM范围内计算。
• Structural and Spectral Analysis of a Mannich Base: 3-(Morpholin-4-ylmethyl)-1,3-Benzothiazole-2-Thione
  作者：S. Franklin、D. Tamilvendan、G. Venkatesa Prabhu、T. Balasubramanian

  DOI：10.1007/s10870-011-0199-z

  日期：2012.1

  The crystal structure of 3-(morpholin-4-ylmethyl)-1,3-benzothiazole-2-thione, C12H14N2OS2, crystallizes in the monoclinic space group (P21/c). This benzothiazole derivative is a mannich base. Methylene group bridges the molecules of 2-mercapto benzothiazole and morpholine with an angle at the methylene bridge being 110.31(12)° [N–C–N]. The dihedral angle between the benzothiazole and morpholine planes is 70.37(5)°. The morpholine ring adopts a chair conformation. The molecular structure is stabilized by the weak C–H···S hydrogen bond in addition to the C–H···π and π···π interactions. Present study reports the conformation and hydrogen bonding interactions. Spectral analysis complement the structure analyzed. The compound 3-(morpholin-4-ylmethyl)-1,3-benzothiazole-2-thione is a Mannich base. The crystal structure gives a picture of a methylene group bridging the molecules of 2-mercapto benzothiazole and morpholine.

  3-(吗啉-4-基甲基)-1,3-苯并噻唑-2-硫酮（C12H14N2OS2）在单斜空间群（P21/c）中的晶体结构。这种苯并噻唑衍生物是一种甘露碱。亚甲基将 2-巯基苯并噻唑和吗啉分子连接起来，亚甲基桥的角度为 110.31(12)° [N-C-N]。苯并噻唑和吗啉平面之间的二面角为 70.37(5)°。吗啉环呈椅状构象。除了 C-H---π 和 π---π 相互作用外，分子结构还通过微弱的 C-H-S 氢键得到稳定。本研究报告了构象和氢键相互作用。光谱分析补充了所分析的结构。3-(吗啉-4-基甲基)-1,3-苯并噻唑-2-硫酮化合物是一种曼尼希碱。晶体结构显示，2-巯基苯并噻唑分子和吗啉分子之间有一个亚甲基桥接。
• A New Approach to the Synthesis of Benzothiazole, Benzoxazole, and Pyridine Nucleosides as Potential Antitumor Agents
  作者：Ahmed I. Khodair、Najim A. Al-Masoudi、Jean-Pierre Gesson

  DOI：10.1081/ncn-120026407

  日期：2003.11

  A modified nitrogen and sulfur glycosylation reaction involving benzothiazole benzoxazole and pyridine nucleoside bases with furanose and pyranose sugars are described. Conformational analysis has been studied by homo- and hetero-nuclear two-dimensional NMR methods (2D DFQ-COSY, HMQC and HMBC). The N and S sites of glycosylation were determined from the H-1, C-13 hetero-nuclear multiple-quantum coherence (HMQC) experiments. All the deprotected nucleosides were tested for their potential antitumor activity.
• Michael and Mannich reactions with benzothiazole-2-thiol
  作者：Adel F. Halasa、George E. P. Smith

  DOI：10.1021/jo00804a006

  日期：1971.3
• Abdel-Rahman, M. A.; Ghattas, A.-B. A. G.; El-Saraf, G. A., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 85, # 1-4, p. 183 - 192
  作者：Abdel-Rahman, M. A.、Ghattas, A.-B. A. G.、El-Saraf, G. A.、Khodary, A.

  DOI：——

  日期：——