N-(5-硝基-2-吡啶基)-1,2,3-噻二唑-4-甲酰胺 | 742097-75-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-(5-硝基-2-吡啶基)-1,2,3-噻二唑-4-甲酰胺
• 英文名称: [1,2,3]Thiadiazole-4-carboxylic acid (5-nitro-pyridin-2-yl)-amide
• 英文别名: N-(5-nitropyridin-2-yl)-1,2,3-thiadiazole-4-carboxamide；N-(5-nitropyridin-2-yl)thiadiazole-4-carboxamide
• CAS: 742097-75-2
• 化学式: C₈H₅N₅O₃S
• 分子量: 251.225
• InChiKey: VDHZZOLZLNEDLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(5-硝基-2-吡啶基)-1,2,3-噻二唑-4-甲酰胺 在 铁粉 、 氯化铵 作用下， 生成 N-(5-isothiocyanatopyridin-2-yl)thiadiazole-4-carboxamide
  参考文献：
  名称：

  Thiourea inhibitors of herpes viruses. Part 2: N-Benzyl-N′-arylthiourea inhibitors of CMV

  摘要：

  A series of highly potent thiourea inhibitors of cytomegalovirus (CMV) with improved stability properties was prepared and evaluated. Compound 29 inhibited the virus in cultured HFF cells with IC50 of 0.2 nM. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.04.093
• 作为产物：
  描述：

  1,2,3-噻重氮-4-酰氯 、 2-氨基-5-硝基吡啶 以 四氢呋喃 为溶剂， 生成 N-(5-硝基-2-吡啶基)-1,2,3-噻二唑-4-甲酰胺
  参考文献：
  名称：

  Thiourea inhibitors of herpes viruses. Part 2: N-Benzyl-N′-arylthiourea inhibitors of CMV

  摘要：

  A series of highly potent thiourea inhibitors of cytomegalovirus (CMV) with improved stability properties was prepared and evaluated. Compound 29 inhibited the virus in cultured HFF cells with IC50 of 0.2 nM. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.04.093

文献信息

• Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
  申请人：American Home Products Corporation

  公开号：US20010039348A1

  公开（公告）日：2001-11-08

  Compounds having the formula: 1 wherein R 1 -R 5 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 carbon members, aryl, heteroaryl, halogen, —CN, —NO 2 , —CO 2 R 6 , —COR 6 , —OR 6 , —SR 6 , —SOR 6 , —SO 2 R 6 , —CONR 7 R 8 , —NR 6 N(R 7 R 8 ), —N(R 7 R 8 ) or W-Y-(CH 2 ) n -Z provided that at least one of R 1 -R 5 is not hydrogen; or R 1 and R 2 or R 3 and R 4 , taken together form a 3 to 7 membered heterocycloalkyl or 3 to 7 membered heteroaryl; R 6 and R 7 are independently hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, or aryl; R 8 is hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 members, aryl or heteroaryl, or R 7 and R 8 , taken together may form a 3 to 7 membered heterocycloalkyl; W is O, NR 6 , or is absent; Y is —(CO)— or —(CO 2 )—, or is absent; Z is alkyl of 1 to 4 carbon atoms, —CN, —CO 2 R 6 , COR 6 , —CONR 7 R 8 , —OCOR 6 , —NR 6 COR 7 , —OCONR 6 , —OR 6 , —SR 6 , —SOR 6 , —SO 2 R 6 , SR6N(R7R8), —N(R 7 R 8 ) or phenyl; G is aryl or fused bicyclic heteroaryl; X is a bond, —NH, alkyl of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, or (CH)J; J is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or benzyl; and n is an integer from 1 to 6; useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.

  化合物的化学式为1，其中R1-R5独立选择自氢、1到6个碳原子的烷基、2到6个碳原子的烯基、2到6个碳原子的炔基、1到6个碳原子的全卤烷基、3到10个碳原子的环烷基、3到10个碳成员的杂环烷基、芳基、杂芳基、卤素、-CN、-NO2、-CO2R6、-COR6、-OR6、-SR6、-SOR6、-SO2R6、-CONR7R8、-NR6N（R7R8）、-N（R7R8）或W-Y-（CH2）n-Z，其中至少一个R1-R5不是氢；或R1和R2或R3和R4，一起形成3到7个成员的杂环烷基或3到7个成员的杂芳基；R6和R7独立地为氢、1到6个碳原子的烷基、1到6个碳原子的全卤烷基或芳基；R8为氢、1到6个碳原子的烷基、1到6个碳原子的全卤烷基、3到10个碳原子的环烷基、3到10个成员的杂环烷基、芳基或杂芳基，或R7和R8一起形成3到7个成员的杂环烷基；W为O、NR6或不存在；Y为-CO-或-CO2-，或不存在；Z为1到4个碳原子的烷基、-CN、-CO2R6、COR6、-CONR7R8、-OCOR6、-NR6COR7、-OCONR6、-OR6、-SR6、-SOR6、-SO2R6、SR6N（R7R8）、-N（R7R8）或苯基；G为芳基或融合的双环杂芳基；X为键、-NH、1到6个碳原子的烷基、1到6个碳原子的烯基、1到6个碳原子的烷氧基、1到6个碳原子的硫代烷基、1到6个碳原子的烷基氨基或（CH）J；J为1到6个碳原子的烷基、3到7个碳原子的环烷基、苯基或苄基；n为1到6的整数。该化合物可用于治疗与疱疹病毒相关的疾病，包括人类巨细胞病毒、单纯疱疹病毒、EB病毒、水痘-带状疱疹病毒、人类疱疹病毒-6和-7以及卡波西疱疹病毒。
• Diaminopyridine-containing thiourea inhibitors of herpes viruses
  申请人：American Home Products Corporation

  公开号：US20030036653A1

  公开（公告）日：2003-02-20

  Compounds of the formula 1 R 1 -R 5 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 carbon members, aryl, heteroaryl, halogen, —CN, —NO 2 , —CO 2 R 6 , —COR 6 , —OR 6 , —SR 6 , —SOR 6 , —SO 2 R 6 , —CONR 7 R 8 , —NR 6 N(R 7 R 8 ), —(R 7 R 8 ) or W—Y—(CH 2 )—Z; or R 2 and R 3 or R 3 and R 4 , taken together form a 3 to 7 membered heterocycloalkyl or 3 to 7 membered heteroaryl; R 6 and R 7 are independently hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, or aryl; R 8 is hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 members, aryl or heteroaryl, or R 7 and R 8 , taken together may form a 3 to 7 membered heterocycloalkyl; A is heteroaryl;

  公式中的化合物1R1-R5独立选择自氢、1至6个碳原子的烷基、2至6个碳原子的烯基、2至6个碳原子的炔基、1至6个碳原子的全卤烷基、3至10个碳原子的环烷基、3至10个碳原子的杂环烷基、芳基、杂芳基、卤素、—CN、—NO2、—CO2R6、—COR6、—OR6、—SR6、—SOR6、—SO2R6、—CONR7R8、—NR6N(R7R8)、—(R7R8)或W—Y—(CH2)—Z；或R2和R3或R3和R4在一起形成3至7个成员的杂环烷基或3至7个成员的杂芳基；R6和R7独立地为氢、1至6个碳原子的烷基、1至6个碳原子的全卤烷基或芳基；R8是氢、1至6个碳原子的烷基、1至6个碳原子的全卤烷基、3至10个碳原子的环烷基、3至10个成员的杂环烷基、芳基或杂芳基，或R7和R8在一起可以形成3至7个成员的杂环烷基；A是杂芳基；
• Aminopyridine-containing thiourea inhibitors of herpes viruses
  申请人：American Home Products Corporation

  公开号：US20020026055A1

  公开（公告）日：2002-02-28

  Compounds of the formula 1 wherein A is heteroaryl; R 9 -R 12 are independently hydrogen, alkyl of 1 to 4 carbon atoms, perhaloalkyl of 1 to 4 carbon atoms, halogen, alkoxy of 1 to 4 carbon atoms, or cyano, or R, and R 10 or R 11 and R 12 may be taken together to form aryl of 5 to 7 carbon atoms; W is O, NR, or is absent; G is aryl or heteroaryl; and X is a bond X is a bond, —NH, alkyl of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, or (CH)J; and J is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or benzyl; and n is an integer from 1 to 6; or a pharmaceutical salt thereof, useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.

  化合物的化学式为1，其中A是杂环芳基；R9-R12独立地是氢、1至4个碳原子的烷基、1至4个碳原子的全氟烷基、卤素、1至4个碳原子的烷氧基或氰基，或者R、R10或R11和R12可以结合形成5至7个碳原子的芳基；W是O、NR或不存在；G是芳基或杂环芳基；X是一个键，—NH、1至6个碳原子的烷基、1至6个碳原子的烯基、1至6个碳原子的烷氧基、1至6个碳原子的硫代烷基、1至6个碳原子的烷基氨基或(CH)J；J是1至6个碳原子的烷基、3至7个碳原子的环烷基、苯基或苄基；n是1至6的整数；或其药物盐，用于治疗与疱疹病毒相关的疾病，包括人类巨细胞病毒、单纯疱疹病毒、Epstein-Barr病毒、水痘-带状疱疹病毒、人类疱疹病毒6和7以及卡波西疱疹病毒。
• Thiourea inhibitors of herpes viruses. Part 2: N-Benzyl-N′-arylthiourea inhibitors of CMV
  作者：Jonathan D. Bloom、Russell G. Dushin、Kevin J. Curran、Fran Donahue、Emily B. Norton、Eugene Terefenko、Thomas R. Jones、Adma A. Ross、Boris Feld、Stanley A. Lang、Martin J. DiGrandi

  DOI：10.1016/j.bmcl.2004.04.093

  日期：2004.7

  A series of highly potent thiourea inhibitors of cytomegalovirus (CMV) with improved stability properties was prepared and evaluated. Compound 29 inhibited the virus in cultured HFF cells with IC50 of 0.2 nM. (C) 2004 Published by Elsevier Ltd.