5-methylpyridine-2-thiocarboxamide | 334017-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-methylpyridine-2-thiocarboxamide
• 英文别名: 5-methyl-2-pyridinecarbothioamide；5-Methylpyridine-2-carbothioamide
• CAS: 334017-98-0
• 化学式: C₇H₈N₂S
• 分子量: 152.22
• InChiKey: BJEVXONLVAPTOY-UHFFFAOYSA-N

物化性质

• 熔点：
  172.5-173 °C
• 沸点：
  291.2±42.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴甲基萘 、 5-methylpyridine-2-thiocarboxamide 以 氯仿 为溶剂， 反应 1.5h， 以65%的产率得到S-(2-naphthylmethyl)-5-methyl-2-pyridylthioimidate hydrobromide
  参考文献：
  名称：

  Diguanidino and “Reversed” Diamidino 2,5-Diarylfurans as Antimicrobial Agents

  摘要：

  Dicationic 2,5-bis(4-guanidinophenyl)furans 5a-5f, 2,5-bis [4-(arylimino)aminophenyl] furans 6a -6b and 6e-6k, and 2,5-bis [4-(alkylimino)aminophenyl] furans 6c -6d have been synthesized starting from 2,5-bis [tri-n-butylstannyl] furan. Thermal melting studies with poly dA . dT and the duplex oligomer d(CGCGAATTCGCG)2 demonstrated high DNA binding affinities for a number of the compounds. The binding affinities are highly dependent on structure and are significantly affected by substituents both on the phenyl rings of the 2,5-diphenylfuran nucleus and on the cationic centers. Of the 17 novel dicationic compounds synthesized, six (6a, 6b, 5b, 6f, 6fi, 6i) exhibited MICs of 2 mug/mL or less versus Mycobacterium tuberculosis. Of the compounds screened against Candida albicans, three gave MICs of 2 mug/mL or less (5b, 6h, Si), and two (5b, 6i) were fungicidal, unlike a standard antifungal drug fluconazole, which was fungistatic. In addition, one of the tested compounds (6i) exhibited a MIC of <1 mug/mL against Aspergillus fumigatus, while also being a fungicidal against this organism. Finally, when evaluated against an expanded fungal panel, compound 6h showed good activity against Cryptococcus neoformans and Rhizopus arrhizus.

  DOI：

  10.1021/jm000413a
• 作为产物：
  描述：

  2-氰基-5-甲基吡啶 在 盐酸 、 硫代乙酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以59%的产率得到5-methylpyridine-2-thiocarboxamide
  参考文献：
  名称：

  Diguanidino and “Reversed” Diamidino 2,5-Diarylfurans as Antimicrobial Agents

  摘要：

  Dicationic 2,5-bis(4-guanidinophenyl)furans 5a-5f, 2,5-bis [4-(arylimino)aminophenyl] furans 6a -6b and 6e-6k, and 2,5-bis [4-(alkylimino)aminophenyl] furans 6c -6d have been synthesized starting from 2,5-bis [tri-n-butylstannyl] furan. Thermal melting studies with poly dA . dT and the duplex oligomer d(CGCGAATTCGCG)2 demonstrated high DNA binding affinities for a number of the compounds. The binding affinities are highly dependent on structure and are significantly affected by substituents both on the phenyl rings of the 2,5-diphenylfuran nucleus and on the cationic centers. Of the 17 novel dicationic compounds synthesized, six (6a, 6b, 5b, 6f, 6fi, 6i) exhibited MICs of 2 mug/mL or less versus Mycobacterium tuberculosis. Of the compounds screened against Candida albicans, three gave MICs of 2 mug/mL or less (5b, 6h, Si), and two (5b, 6i) were fungicidal, unlike a standard antifungal drug fluconazole, which was fungistatic. In addition, one of the tested compounds (6i) exhibited a MIC of <1 mug/mL against Aspergillus fumigatus, while also being a fungicidal against this organism. Finally, when evaluated against an expanded fungal panel, compound 6h showed good activity against Cryptococcus neoformans and Rhizopus arrhizus.

  DOI：

  10.1021/jm000413a

文献信息

• Synthesis and antimicrobial activity of novel dicationic "reversed amidines"
  申请人：——

  公开号：US20040235927A1

  公开（公告）日：2004-11-25

  The present invention relates to novel 2,5-bis{[alkyl (or aryl) imino]aminophenyl}furans and thiophenes of the general formula 1 in which R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R 5 is H, alkyl or aryl; R 6 is H, alkyl, aryl, or NR 7 R 8 , in which R 7 and R 8 are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR 9 , in which R 9 is H or alkyl, and to the use of such compounds.

  本发明涉及新型的2,5-双{[烷基（或芳基）亚胺]氨基苯基}呋喃和噻吩，其通式为1，其中R1、R2、R3和R4各自独立地选自H、烷基、烷氧基、卤素和烷基卤素基团；R5为H、烷基或芳基；R6为H、烷基、芳基或NR7R8，其中R7和R8各自独立地选自H、烷基和芳基；X为O、S或NR9，其中R9为H或烷基，并且涉及这种化合物的用途。
• Synthesis and antimicrobial activity of novel dicationic"reversed amidines"
  申请人：——

  公开号：US20030083362A1

  公开（公告）日：2003-05-01

  The present invention relates to novel 2,5-bis {[alkyl (or aryl) imino] aminophenyl} furans and thiophenes of the general formula 1 in which R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R 5 is H, alkyl or aryl; R 6 is H, alkyl, aryl, or NR 7 R 8 , in which R 7 and R 8 are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR 9 , in which R 9 is H or alkyl, and to the use of such compounds.

  本发明涉及一种新型的2,5-双{[烷基（或芳基）亚胺]氨基苯基呋喃和噻吩，其通式为1，其中R1、R2、R3和R4分别独立地选自H、烷基、烷氧基、卤素和烷基卤素基团；R5为H、烷基或芳基；R6为H、烷基、芳基或NR7R8，其中R7和R8分别独立地选自H、烷基和芳基；X为O、S或NR9，其中R9为H或烷基，并且涉及这些化合物的使用。
• Synthesis and antimicrobial activity of novel dicationic ''reversed amidines''
  申请人：Boykin W. David

  公开号：US20080058372A1

  公开（公告）日：2008-03-06

  The present invention relates to novel 2,5-bis[alkyl(or aryl)imino]aminophenyl}furans and thiophenes of the general formula in which R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R 5 is H, alkyl or aryl; R 6 is H, alkyl, aryl, or NR 7 R 8 , in which R 7 and R 8 are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR 9 , in which R 9 is H or alkyl, and to the use of such compounds.

  本发明涉及一种新型的2,5-双[烷基（或芳基）亚胺基]氨基苯基}呋喃和噻吩，其一般式如下：其中R1、R2、R3和R4各自独立地选自H、烷基、烷氧基、卤素和烷基卤素基团；R5为H、烷基或芳基；R6为H、烷基、芳基或NR7R8，其中R7和R8各自独立地选自H、烷基和芳基；X为O、S或NR9，其中R9为H或烷基，以及这些化合物的使用。
• CARBOXYLIC ACID DERIVATIVES AND DRUGS CONTAINING THE SAME
  申请人：Eisai Co., Ltd.

  公开号：EP1216980A1

  公开（公告）日：2002-06-26

  The present invention provides a novel carboxylic acid compound, a salt thereof or a hydrate of them useful as an insulin-resistant improver, and a medicament comprising the compound as an active ingredient. That is, the present invention provides a carboxylic acid compound represented by the following formula (I), a salt thereof, an ester thereof or a hydrate of them. In the formula, R1 represents hydrogen atom, hydroxyl group or a C1-6 alkyl group etc. which may have one or more substituents; L represents a single or double bond or a C1-6 alkylene group etc. which may have one or more substituents; M represents a single bond or a C1-6 alkylene group etc. which may have one or more substituents; T represents a single bond or a C1-3 alkylene group which may have one or more substituents; W represents carboxyl group or a group represented by the formula -CON(Rw1)Rw2 (wherein Rw1 and Rw2 are the same as or different from each other and each represents hydrogen atom, formyl group etc.) etc.; represents a single or double bond; X represents oxygen atom or a C2-6 alkenylene group etc. which may have one or more substituents; Y represents a C5-12 aromatic hydrocarbon group etc. which may have one or more substituents and which may have one or more heteroatoms; and ring Z represents a C5-6 aromatic hydrocarbon group which may have 0 to 4 substituents and which may have one or more heteroatoms.

  本发明提供了一种新型羧酸化合物、其盐或它们的水合物，可用作胰岛素抗性改进剂，以及包含该化合物作为活性成分的药物。也就是说，本发明提供了由下式（I）代表的羧酸化合物、其盐、酯或它们的水合物。 式中，R1 代表氢原子、羟基或 C1-6 烷基等，可有一个或多个取代基；L 代表单键或双键或 C1-6 亚烷基等，可有一个或多个取代基；M 代表单键或 C1-6 亚烷基等，可有一个或多个取代基。W 代表羧基或由式-CON(Rw1)Rw2 所代表的基团（其中 Rw1 和 Rw2 彼此相同或不同，且各自代表氢原子、甲酰基等）等。)等表示的基团；代表单键或双键；X 代表氧原子或 C2-6 烯基等，可有一个或多个取代基；Y 代表 C5-12 芳烃基等，可有一个或多个取代基，可有一个或多个杂原子；环 Z 代表 C5-6 芳烃基，可有 0 至 4 个取代基，可有一个或多个杂原子。
• SYNTHESIS AND ANTIMICROBIAL ACTIVITYOF NOVEL DICATIONIC "REVERSED AMIDINES"
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1337510A2

  公开（公告）日：2003-08-27