5-(thiophen-2-yl)-1,3,4-thiadiazole-2-thiol | 41526-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(thiophen-2-yl)-1,3,4-thiadiazole-2-thiol
• 英文别名: 2-(2-Thienyl)-5-thio-1,3,4-thiadiazol (IIIa)；5-thiophen-2-yl-3H-[1,3,4]thiadiazole-2-thione；5-thiophen-2-yl-3H-1,3,4-thiadiazole-2-thione
• CAS: 41526-33-4
• 化学式: C₆H₄N₂S₃
• 分子量: 200.309
• InChiKey: OPZYRKWLFVOZTN-UHFFFAOYSA-N

物化性质

• 沸点：
  311.2±34.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴苯乙酮 、 5-(thiophen-2-yl)-1,3,4-thiadiazole-2-thiol 以 乙醇 为溶剂， 生成 2-(2-Thienyl)-5-phenylthiazolo2,3-b>-1,3,4-thiadiazol (V)
  参考文献：
  名称：

  双环噻二唑。I.2-（2-噻吩基）-5-苯基噻唑（2,3-b）-1,3,4-噻二唑。

  摘要：

  DOI：

  10.1002/jps.2600620239
• 作为产物：
  描述：

  potassium N'-(thiophene-2-carbonyl) hydrazine carbodithioate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 5-(thiophen-2-yl)-1,3,4-thiadiazole-2-thiol
  参考文献：
  名称：

  双环噻二唑。I.2-（2-噻吩基）-5-苯基噻唑（2,3-b）-1,3,4-噻二唑。

  摘要：

  DOI：

  10.1002/jps.2600620239

文献信息

• Unfused Heterobicycles as Amplifiers of Phleomycin. VII> Some Bithiazoles; Thienyl-, Furanyl- and Thiazolyl-thiadiazoles and Related Oxadiazoles
  作者：WB Cowden、SJ Sullivan、DJ Brown

  DOI：10.1071/ch9851257

  日期：——

  Syntheses are described for several unfused heterobicycles including 4,5′- and 2,4′-bithiazoles, 5-(thiazol-4′ and 5′-yl)-1,3,4- thiadiazoles , 5-(thien-2′-yl)-, 5-(furan-2′ and 3′-yl)-, thiadiazoles and related oxadiazoles, all with side chains containing dialkylamine terminal groups. The activities of these compounds as amplifiers of phleomycin -G are reported.

  介绍了几种未融合杂环的合成方法，包括 4,5′- 和 2,4′- 双噻唑、5-(噻唑-4′和 5′-基)-1,3,4-噻二唑、5-(噻吩-2′-基)-、5-(呋喃-2′和 3′-基)-、噻二唑和相关的噁二唑，所有侧链都含有二烷基胺末端基团。报告了这些化合物作为博来霉素-G 放大剂的活性。
• Synthesis and antibacterial activity of novel lincomycin derivatives. II. Exploring (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives
  作者：Ko Kumura、Yoshinari Wakiyama、Kazutaka Ueda、Eijiro Umemura、Takashi Watanabe、Megumi Kumura、Takuji Yoshida、Keiichi Ajito

  DOI：10.1038/ja.2016.139

  日期：2017.5

  The synthesis and antibacterial activity of (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives are described. These derivatives were mainly prepared by the Mitsunobu reaction of 2,3,4-tris-O-(trimethylsilyl)lincomycin and the corresponding thiols. Exploring structure-activity relationships of the substituent at the 5 position of a thiadiazole ring revealed that compounds with

  描述了（7S）-7-（5-芳基-1,3,4-噻二唑-2-基-硫基）-7-脱氧林可霉素衍生物的合成和抗菌活性。这些衍生物主要是通过2,3,4-三-O-（三甲基甲硅烷基）林可霉素与相应的硫醇的Mitsunobu反应制备的。探索噻二唑环的5位上的取代基的构效关系，发现具有邻位取代苯基的化合物与具有未取代的报道的化合物（1）相比，具有erm基因的肺炎链球菌和化脓性链球菌显示出改善的抗菌活性。苯环。
• Nematicidal compositions
  申请人：Ciba-Geigy Corporation

  公开号：US04861787A1

  公开（公告）日：1989-08-29

  Novel compounds of the formula ##STR1## in which R' represents C.sub.1 -C.sub.5 -alkyl, halogen, trifluoromethyl or C.sub.1 -C.sub.3 -alkoxy; R" represents C.sub.1 -C.sub.5 -alkyl or halogen; and R"' represents C.sub.1 -C.sub.5 -alkyl that is unsubstituted or is substituted by from 1 to 6 halogen atoms, C.sub.1 -C.sub.5 -alkenyl that is unsubstituted or is substituted by from 1 to 6 halogen atoms, or C.sub.1 -C.sub.5 - alkynyl that is unsubstituted or is substituted by from 1 to 6 halogen atoms; m represents 0, 1, 2 or 3 and n represents 0 or 1; and X.sub.1 and X.sub.2 each represents, independently of the other, oxygen or sulphur, as active ingredients for controlling plant parasite nematodes and for preventing damage to cultivated plants caused by nematode attack.

  化合物的新颖配方式为 ##STR1## 其中R'代表C.sub.1-C.sub.5-烷基，卤素，三氟甲基或C.sub.1-C.sub.3-烷氧基；R"代表C.sub.1-C.sub.5-烷基或卤素；R"'代表未取代或被1至6个卤素原子取代的C.sub.1-C.sub.5-烷基，未取代或被1至6个卤素原子取代的C.sub.1-C.sub.5-烯基或未取代或被1至6个卤素原子取代的C.sub.1-C.sub.5-炔基；m代表0、1、2或3，n代表0或1；X.sub.1和X.sub.2分别独立地代表氧或硫，作为控制植物寄生线虫和预防线虫攻击对栽培植物造成损害的有效成分。
• Lincomycin Derivatives and Antimicrobial Agents Comprising the Same as Active Ingredient
  申请人：Umemura Eijirou

  公开号：US20090156512A1

  公开（公告）日：2009-06-18

  This invention provides compounds of formula (I) or its pharmacologically acceptable salt or solvate, wherein A represents aryl or a monocyclic or bicyclic heterocyclic group, R 1 represents a halide, nitro, substituted C 1-6 alkyl, optionally substituted amino, C 1-6 alkyloxycarbonyl, optionally substituted aryl, a heterocyclic group, or heterocyclic carbonyl, R 2 represents a hydrogen atom or C 1-6 alkyl, R 3 represents C 1-6 alkyl, all of R 4 , R 5 , and R 6 represent a hydrogen atom, R 7 represents C 1-6 alkyl, m is 1 or 2, and n is 1. The compounds are novel lincomycin derivatives having a potent activity against resistant pneumococci. The compounds can be used as an antimicrobial agent and are useful for preventing or treating bacterial infectious diseases.

  本发明提供了式（I）的化合物或其药理学上可接受的盐或溶剂，其中A代表芳基或单环或双环杂环基，R1代表卤素、硝基、取代的C1-6烷基、可选取代的氨基、C1-6烷氧羰基、可选取代的芳基、杂环基或杂环羰基，R2代表氢原子或C1-6烷基，R3代表C1-6烷基，R4、R5和R6均代表氢原子，R7代表C1-6烷基，m为1或2，n为1。这些化合物是新型的林可霉素衍生物，对耐药性肺炎球菌具有强大的活性。这些化合物可以用作抗微生物剂，并且对于预防或治疗细菌感染性疾病是有用的。
• 2,3-(dihydro)bicyclic pyrazolidinones
  申请人：ELI LILLY AND COMPANY

  公开号：EP0203723A1

  公开（公告）日：1986-12-03

  2,3-(Dihydro) bicyclic pyrazolidinones are intermediates for bicyclic pyrazolidinone antimicrobials. The intermediates have the formula wherein: either R1 or R2 is hydrogen, C1 to C6 alkyl, C1 to C6 substituted alkyl, perfluoro C2 to C4 alkyl, C7 to C12 alkylaryl, C7 to C12 substituted alkylaryl, phenyl, substituted phenyl or cyano; a group of the formula wherein X is fluoro, chloro, bromo or iodo; a group of the formula wherein z is 0, 1 or 2 and R5 is C, to C6 alkyl, C1 to C6 substituted alkyl, phenyl, substituted phenyl, C7 to C12 alkylaryl, C7 to C12 substituted alkylaryl or a heterocyclic ring; a group of the formula wherein R6 is hydrogen, C1 to C6 alkyl, C1 to C6 substituted alkyl, perfluoro C2 to C4 alkyl, trihalomethyl, C7 to C12 alkylaryl, C7 to C12 substituted alkylaryl, phenyl or substituted phenyl; a group of the formula wherein R7 is hydrogen, an organic or inorganic cation, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 alkylaryl, C7 to C12 substituted alkylaryl, phenyl, substituted phenyl, a carboxy protecting group, or a non-toxic, metabolically-labile ester-forming group; or a group of the formula -CH2-S-Heterocyclic ring and the other of Rt or R2 is a group of the formula wherein R8 is hydrogen, an organic or inorganic cation, a carboxy protecting group or a non-toxic, metabolically-labile ester-forming group; R3 and R4 are the same or different and are hydrogen, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 alkylaryl, C7 to C12 substituted alkylaryl, phenyl, substituted phenyl or a group of the formula wherein R9 has the same definition as R7; Y is C1 to C6 alkyl, C1 to C6 substituted alkyl, phenyl, substituted phenyl, C7 to C12 alkylaryl or C7 to C12 substituted alkylaryl; or a pharmaceutically acceptable salt thereof.

  2,3-（二氢）双环吡唑烷酮是双环吡唑烷酮抗菌剂的中间体。这些中间体的化学式为 其中 R1 或 R2 为氢、C1 至 C6 烷基、C1 至 C6 取代烷基、全氟 C2 至 C4 烷基、C7 至 C12 烷芳基、C7 至 C12 取代烷芳基、苯基、取代苯基或氰基； 式中的基团 其中 X 为氟、氯、溴或碘； 式中 X 为氟、氯、溴或碘的基团 其中 z 是 0、1 或 2，R5 是 C 至 C6 烷基、C1 至 C6 取代的烷基、苯基、取代的苯基、C7 至 C12 烷芳基、C7 至 C12 取代的烷芳基或杂环； 式中的基团 其中 R6 是氢、C1 至 C6 烷基、C1 至 C6 取代的烷基、全氟 C2 至 C4 烷基、三卤甲基、C7 至 C12 烷芳基、C7 至 C12 取代的烷芳基、苯基或取代的苯基； 式中的基团 其中 R7 是氢、有机或无机阳离子、C1 至 C6 烷基、C1 至 C6 取代的烷基、C7 至 C12 烷芳基、C7 至 C12 取代的烷芳基、苯基、取代的苯基、羧基保护基团或无毒、代谢上易腐烂的成酯基团；或式中的基团 -CH2-S-杂环，而 Rt 或 R2 的另一个是式中的基团 其中 R8 是氢、有机或无机阳离子、羧基保护基团或无毒、代谢上易消化的成酯基团； R3 和 R4 相同或不同，并且是氢、C1 至 C6 烷基、C1 至 C6 取代烷基、C7 至 C12 烷芳基、C7 至 C12 取代烷芳基、苯基、取代苯基或式中的基团 其中 R9 的定义与 R7 相同； Y 是 C1 至 C6 烷基、C1 至 C6 取代的烷基、苯基、取代的苯基、C7 至 C12 烷芳基或 C7 至 C12 取代的烷芳基；或其药学上可接受的盐。