1-methyl-5-(phenylthio)-1H-tetrazole

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methyl-5-(phenylthio)-1H-tetrazole
• 英文别名: 1-methyl-5-phenylthio-1,2,3,4-tetrazole；1-Methyl-5-thiobenzyltetrazole；1-methyl-5-phenylsulfanyltetrazole
• 化学式: C₈H₈N₄S
• 分子量: 192.244
• InChiKey: PNZNOIVKLPJBOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-5-(phenylthio)-1H-tetrazole 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以63%的产率得到1-methyl-5-(phenylsulfonyl)-1H-tetrazole
  参考文献：
  名称：

  Tetrazoles: LVII. Preparation and chemical properties of 1-substituted 5-arylsulfonyltetrazoles

  摘要：

  Oxidation of 1-substituted 5-arylsulfanyltetrazoles with m-chloroperoxybenzoic acid and NaIO4 in the presence of RuCl3 leads to the formation of the 5-arylsulfonyltetrazoles. The microwave activation significantly accelerates the oxidation with sodium periodate. The phenylsulfonyl group in compounds obtained underwent the nucleophilic substitution when treated with ethanol, phenol, or benzimidazole in acetonitrile in the presence of NaOH.

  DOI：

  10.1134/s1070428013050229
• 作为产物：
  描述：

  苯硫酚 在 hydridotetakis(triphenylphosphine)rhodium(I) 、 三乙胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 氯苯 、 乙腈 为溶剂， 反应 3.0h， 生成 1-methyl-5-(phenylthio)-1H-tetrazole
  参考文献：
  名称：

  α-（苯硫基）异丁苯酮的铑催化杂芳族化合物的苯硫基化反应

  摘要：

  在催化量的RhH（PPh 3）4和1,2-双（二苯基膦基）乙烷（dppe）存在下，1,3-苯并噻唑，1,3-苯并恶唑和苯并噻吩与α-（苯硫基）异丁酮反应2-苯硫基衍生物。反应性单环杂芳族化合物，1-甲基-1,2,3,4-四唑和2-氰基噻吩也被转化为5-苯硫基衍生物。使用适当的苯硫基转移试剂对于将杂芳族C–H键有效催化转化为C–S键至关重要。

  DOI：

  10.1016/j.tetlet.2011.02.077

文献信息

• WATER-SOLUBLE CAMPTOTHECIN DERIVATIVE, PHARMACEUTICAL COMPOSITION AND USE THEREOF
  申请人：Zhou Wenqiang

  公开号：US20140155336A1

  公开（公告）日：2014-06-05

  The present invention relates to a water soluble derivative of camptothecin and preparation method thereof, the derivative having a structure of formula I and being appropriate in water solubility, and having anti-cancer activity and stability of lactonic ring. The present invention also relates to a method for synthesizing the compound and medical use of the compound.

  本发明涉及一种水溶性紫杉醇衍生物及其制备方法，所述衍生物具有式I的结构，在水溶性方面适宜，并具有抗癌活性和内酯环的稳定性。本发明还涉及一种合成该化合物的方法以及该化合物的医药用途。
• CAMPTOTHECIN DERIVATIVE, AND PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION AND APPLICATION
  申请人：Zhou Wenqiang

  公开号：US20140107342A1

  公开（公告）日：2014-04-17

  The present invention relates to a camptothecin derivative having a structure as represented by Formula (II), in which X n+ is selected from H + , K + , Na + , Li + , Mg 2+ , Ca 2+ , Zn 2+ , Fe 3+ , and ammonium ion, while R 1 , R 2 , R 3 , and R 4 independently represent a hydrogen, a hydroxyl group, a nitro group, a cyano group, a halogen, a carboxyl group, an optionally substituted amino group, a silicon-containing group, a monocyclic aryloxy group, an optionally substituted C1-C6 alkoxy group, an optionally substituted C1-C6 alkylcarbonyl group, an optionally substituted C1-C6 alkyl group, or an optionally substituted C3-C6 cycloalkyl group; alternatively, R 1 and R 2 are connected via one to three other atoms to form a heterocyclic ring; and in another embodiment, R 3 and R 4 are oxygen atoms and connected via —O—(CH 2 ) n —O—, forming a ring, in which n=I or 2. The compound has great water-solubility, chemical stability, and great efficacy in treatment on cancer.

  本发明涉及一种具有如下式（II）所表示结构的紫杉醌衍生物，其中X n+ 选自H + 、K + 、Na + 、Li + 、Mg 2+ 、Ca 2+ 、Zn 2+ 、Fe 3+ 和铵离子，而R 1 、R 2 、R 3 和R 4 独立地代表氢、羟基、硝基、氰基、卤素、羧基、可选择取代的氨基、含硅基团、单环芳氧基团、可选择取代的C1-C6烷氧基团、可选择取代的C1-C6烷基羰基团、可选择取代的C1-C6烷基团，或可选择取代的C3-C6环烷基团；或者，R 1 和R 2 通过一到三个其他原子连接形成杂环环；在另一实施例中，R 3 和R 4 是氧原子，并通过—O—(CH 2 ) n —O—连接形成一个环，其中n=1或2。该化合物具有很高的水溶性、化学稳定性，并在癌症治疗中具有很高的功效。
• Mild ligand-free Cu0-catalyzed chemoselective S-arylation of 2-mercaptoimidazole at low catalyst loading
  作者：Bryan Yong-Hao Tan、Yong-Chua Teo

  DOI：10.1016/j.tet.2016.08.085

  日期：2016.10

  2-mercaptoimidazole derivatives with a series of with differently substituted iodobenzenes and iodothiophenes at 100 °C is described. This method proceeds efficiently without ligands and at low catalyst loading (3 mol %), without the need for stringent inert conditions. Under optimized conditions, the S-arylated products were obtained in good yields of up to 90%.

  描述了一种温和的方法，用于在100°C下用Cu 0催化2-巯基咪唑衍生物与一系列不同取代的碘代苯和碘代噻吩的化学选择性C S交叉偶联。该方法无需配体且催化剂负载量低（3 mol％）即可高效进行，而无需严格的惰性条件。在优化的条件下，可以高达90％的高收率获得S-芳基化产物。
• Efficient copper-catalyzed C–S cross-coupling of heterocyclic thiols with aryl iodides
  作者：Liang-Feng Niu、Yan Cai、Chao Liang、Xin-Ping Hui、Peng-Fei Xu

  DOI：10.1016/j.tet.2011.02.064

  日期：2011.4

  A copper-catalyzed cross-coupling of heterocyclic thiols with aryl iodides is reported. The reaction was carried out in the presence of CuI (5 mol %), 1,10-phenanthroline (10 mol %) and K2CO3 (1.3 equiv) in DMF at 120 °C. A variety of heterocyclic sulfides were prepared in high selectivities and yields.

  据报道，铜催化的杂环硫醇与芳基碘化物的交叉偶联。反应在120℃下在CuI（5mol％），1，10-菲咯啉（10mol％）和K 2 CO 3（1.3当量）的存在下在DMF中进行。以高选择性和高产率制备了各种杂环硫化物。
• Substituted N-methylene derivatives of thienamycin sulfoxide and sulfone and their preparation
  申请人：Merck & Co., Inc.

  公开号：EP0001264A1

  公开（公告）日：1979-04-04

  Disclosed are substituted N-methylene derivatives of thienamycin sulfoxide (1, n=1) and sulfone (I, n=2) which may be represented by the following structural formula: wherein X and Y are selected from the group consisting of hydrogen, R, OR, SR, and NR' R2 wherein, inter alia, R is substituted or unsubstituted: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl, and heterocyclylalkyl; R1 and R2 are hydrogen or R. Such compounds and their pharmaceutically acceptable salt, ether, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  本发明公开了噻喃霉素亚砜（1，n=1）和砜（I，n=2）的取代 N-亚甲基衍生物，其结构式如下： 其中 X 和 Y 选自由氢、R、OR、SR 和 NR' R2 组成的组，其中除其他外，R 是取代或未取代的：烷基、烯基、炔基、环烷基、环烷基烷基、芳基、芳烷基、杂芳基、杂芳基烷基、杂环烷基和杂环烷基；R1 和 R2 是氢或 R。此类化合物及其药学上可接受的盐、醚、酯和酰胺衍生物可用作抗生素。此外，还公开了制备此类化合物的工艺；包含此类化合物的药物组合物；以及治疗方法，包括在需要抗生素效果时施用此类化合物和组合物。