5-{5-(methylamino)thiazol-4-yl}-1,3,4-thiadiazole-2-thiol | 1088410-95-0

• 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-{5-(methylamino)thiazol-4-yl}-1,3,4-thiadiazole-2-thiol
• 英文别名: 5-[5-(methylamino)-1,3-thiazol-4-yl]-3H-1,3,4-thiadiazole-2-thione
• CAS: 1088410-95-0
• 化学式: C₆H₆N₄S₃
• 分子量: 230.338
• InChiKey: VJZOEYKUAYGHQW-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-N-((2S,4R)-1-(tert-butoxycarbonyl)-4-(cyclopropylmethyl)piperidine-2-carbonyl)-1-thio-α-lincosamide 、 5-{5-(methylamino)thiazol-4-yl}-1,3,4-thiadiazole-2-thiol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 以81%的产率得到methyl 6-N-((2S,4R)-1-tert-butoxycarbonyl-4-cyclopropylmethyl-pipecolyl)-7-deoxy-7-epi-7-(5-(4-(methylamino)thiazol-4-yl)-1,3,4-thiadiazol-2-ylthio)-1-thio-α-lincosamide
  参考文献：
  名称：

  EP2166015

  摘要：

  公开号：

文献信息

• Synthesis and structure–activity relationships of novel lincomycin derivatives. Part 4: synthesis of novel lincomycin analogs modified at the 6- and 7-positions and their potent antibacterial activities
  作者：Yoshinari Wakiyama、Ko Kumura、Eijiro Umemura、Kazutaka Ueda、Takashi Watanabe、Keiko Yamada、Takafumi Okutomi、Keiichi Ajito

  DOI：10.1038/ja.2017.54

  日期：2017.8

  To modify lincomycin (LCM) at the C-6 and the C-7 positions, we firstly prepared various substituted proline intermediates (7, 11-15 and 17). These proline intermediates were coupled with methyl 1-thio-α-lincosamide and tetrakis-O-trimethylsilylation followed by selective deprotection of the TMS group at the 7-position gave a wide variety of key intermediates (23-27, 47 and 50). Then, we synthesized

  为了在C-6和C-7位置修饰林可霉素（LCM），我们首先制备了各种取代的脯氨酸中间体（7、11-15和17）。这些脯氨酸中间体与1-硫代-α-lincosamide甲基和四-O-三甲基甲硅烷基化偶合，然后在7位选择性脱保护TMS基团，得到各种各样的关键中间体（23-27、47和50）。然后，我们合成了应用Mitsunobu反应（S N）在7位修饰的各种新型LCM类似物2反应和Pd催化的交叉偶联反应。与相应的1'-N-甲基衍生物（3和37）相比，化合物34和35（1'-NH衍生物）对具有erm基因的抗性病原体表现出增强的抗菌活性。根据已报道的SAR，我们修饰了在C-7位置具有5-（2-硝基苯基）-1,3,4-噻二唑-2-基的LCM衍生物的4'-位。化合物56对带有erm基因的肺炎链球菌和化脓性链球菌显示出显着的强效抗菌活性，并且与34和57相比，具有针对erm基因的肺炎链球菌的活性得到了改善
• LINCOSAMIDE DERIVATIVES AND ANTIMICROBIAL AGENTS COMPRISING THE SAME AS ACTIVE INGREDIENT
  申请人：Umemura Eijirou

  公开号：US20100184746A1

  公开（公告）日：2010-07-22

  An objective of the present invention is to provide compounds of formula (I) or their pharmacologically acceptable salts or solvates wherein A represents aryl while R 1 represents a five- or six-membered monocyclic heterocyclic group, or A represents a four- to six-membered monocyclic heterocyclic group while R 1 represents aryl or a five- or six-membered monocyclic heterocyclic group; R 2 represents a hydrogen atom or C 1-6 alkyl; R 3 represents C 1-6 alkyl or C 3-6 cycloalkyl-C 1-4 alkyl; R 4 , R 5 , and R 6 represent a hydrogen atom; R 7 represents C 1-6 alkyl; and m is 1 to 3. The compounds are novel lincosamide derivatives that have a potent activity against resistant Streptococcus pneumoniae . Further, the compounds are usable as antimicrobial agents and are useful for preventing or treating bacterial infectious diseases.

  本发明的目标是提供式（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，而R1代表五元或六元单环杂环基，或A代表四至六元单环杂环基，而R1代表芳基或五元或六元单环杂环基；R2代表氢原子或C1-6烷基；R3代表C1-6烷基或C3-6环烷基-C1-4烷基；R4、R5和R6代表氢原子；R7代表C1-6烷基；m为1至3。这些化合物是新型的林可霉素衍生物，对耐药性肺炎链球菌具有强效活性。此外，这些化合物可用作抗微生物剂，对预防或治疗细菌感染性疾病有用。
• 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。
• LINCOMYCIN DERIVATIVE AND ANTIBACTERIAL AGENT CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：EP1970377A1

  公开（公告）日：2008-09-17

  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, R1 represents a halide, nitro, substituted C1-6 alkyl, optionally substituted amino, C1-6 alkyloxycarbonyl, optionally substituted aryl, a heterocyclic group, or heterocyclic carbonyl, R2 represents a hydrogen atom or C1-6 alkyl, R3 represents C1-6 alkyl, all of R4, R5, and R6 represent a hydrogen atom, R7 represents C1-6 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)化合物或其药理学上可接受的盐或溶液，其中 A 代表芳基或单环或双环杂环基团，R1 代表卤化物、硝基、取代的 C1-6 烷基、任选取代的氨基、任选取代的 C1-6 烷氧羰基、任选取代的芳基、杂环基团或杂环羰基，R2 代表氢原子或 C1-6 烷基，R3 代表 C1-6 烷基，R4 代表 C1-6 烷基，R5 代表 C1-6 烷基、C1-6烷氧基羰基、任选取代的芳基、杂环基团或杂环羰基，R2代表氢原子或C1-6烷基，R3代表C1-6烷基，所有R4、R5和R6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效活性。这些化合物可用作抗菌剂，用于预防或治疗细菌性传染病。
• LINCOSAMIDE DERIVATIVE, AND ANTIBACTERIAL AGENT COMPRISING THE SAME AS ACTIVE INGREDIENT
  申请人：Meiji Seika Kaisha Ltd.

  公开号：EP2166015A1

  公开（公告）日：2010-03-24

  An objective of the present invention is to provide compounds of formula (I) or their pharmacologically acceptable salts or solvates wherein A represents aryl while R1 represents a five- or six-membered monocyclic heterocyclic group, or A represents a four- to six-membered monocyclic heterocyclic group while R1 represents aryl or a five- or six-membered monocyclic heterocyclic group; R2 represents a hydrogen atom or C1-6 alkyl; R3 represents C1-6 alkyl or C3-6 cycloalkyl-C1-4 alkyl; R4, R5, and R6 represent a hydrogen atom; R7 represents C1-6 alkyl; and m is 1 to 3. The compounds are novel lincosamide derivatives that have a potent activity against resistant Streptococcus pneumoniae. Further, the compounds are usable as antimicrobial agents and are useful for preventing or treating bacterial infectious diseases.

  本发明的目的是提供式(I)化合物或其药理学上可接受的盐或溶液，其中 A 代表芳基，而 R1 代表五元或六元单环杂环基团，或 A 代表四至六元单环杂环基团，而 R1 代表芳基或五元或六元单环杂环基团；R2代表氢原子或C1-6烷基；R3代表C1-6烷基或C3-6环烷基-C1-4烷基；R4、R5和R6代表氢原子；R7代表C1-6烷基；m为1至3。这些化合物是新型林可酰胺衍生物，对耐药性肺炎链球菌具有强效活性。此外，这些化合物还可用作抗菌剂，用于预防或治疗细菌感染性疾病。