2,3-diamino-6,7-dichloronaphthalene | 197973-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-diamino-6,7-dichloronaphthalene
• 英文别名: 6,7-Dichloronaphthalene-2,3-diamine
• CAS: 197973-63-0
• 化学式: C₁₀H₈Cl₂N₂
• 分子量: 227.093
• InChiKey: FLBOQERHBQNPDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-diamino-6,7-dichloronaphthalene 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 45.0h， 生成 6,7-dichloro-2-methylthio-1-(β-D-ribofuranosyl)naphtho[2,3-d]imidazole
  参考文献：
  名称：

  Synthesis of 2,6,7-Trichloro-1-(β-d-ribofuranosyl)naphtho[2,3-d]imidazole:  A Linear Dimensional Analogue of the Antiviral Agent TCRB

  摘要：

  Human cytomegalovirus (HCMV) remains a significant clinical problem in neonates and immunocompromised individuals such as those undergoing transplantation as well as individuals with acquired immune deficiency syndrome (AIDS). Recently in our laboratory, 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB, 1a) and 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BDCRB, 1b) were found to have better activities in cell culture studies against HCMV than the clinically used agents ganciclovir and foscarnet. These benzimidazole compounds appear to act by a unique mechanism. However, as the biological target of TCRB and BDCRB has not been completely identified, 2,6,7-trichloro-1-(beta-D-ribofuranosyl)naphthol[2,3-d]imidazole (2) was designed as a linear dimensional analogue of TCRB for a study on the spatial limitation of the binding site in the target enzyme. In the synthesis, a convenient route was developed for the synthesis of 2-substituted 6,7-dichloronaphtho[2,3-d]imidazoles involving a Diels-Alder reaction of 4,5-dichloro-o-quinodimethane (8) as the key step. 6,7-Dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide (15) was found to be an ideal precursor for the generation of the elusive intermediate 8. The ribosylation of 6,7-dichloronaphtho[2,3-d]imidazoles was influenced by the functional group at the 2-position and 6,7-dichloro-2-methylthionaphtho[2,3-d]imidazole (3c) was found to smoothly undergo ribosylation. The 2-methylthio group of the unprotected nucleoside 25 was converted into a chloro group under mild conditions to give nucleoside 2 in high yield.

  DOI：

  10.1021/jo971152o
• 作为产物：
  描述：

  6,7-Dichloro-3-nitro-naphthalene-2-carboxylic acid ethyl ester 在 镍 sodium hydroxide 、 叠氮磷酸二苯酯 、 水 、 氢气 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 25.0~100.0 ℃ 、275.79 kPa 条件下， 反应 25.0h， 生成 2,3-diamino-6,7-dichloronaphthalene
  参考文献：
  名称：

  Synthesis of 2,6,7-Trichloro-1-(β-d-ribofuranosyl)naphtho[2,3-d]imidazole:  A Linear Dimensional Analogue of the Antiviral Agent TCRB

  摘要：

  Human cytomegalovirus (HCMV) remains a significant clinical problem in neonates and immunocompromised individuals such as those undergoing transplantation as well as individuals with acquired immune deficiency syndrome (AIDS). Recently in our laboratory, 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB, 1a) and 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BDCRB, 1b) were found to have better activities in cell culture studies against HCMV than the clinically used agents ganciclovir and foscarnet. These benzimidazole compounds appear to act by a unique mechanism. However, as the biological target of TCRB and BDCRB has not been completely identified, 2,6,7-trichloro-1-(beta-D-ribofuranosyl)naphthol[2,3-d]imidazole (2) was designed as a linear dimensional analogue of TCRB for a study on the spatial limitation of the binding site in the target enzyme. In the synthesis, a convenient route was developed for the synthesis of 2-substituted 6,7-dichloronaphtho[2,3-d]imidazoles involving a Diels-Alder reaction of 4,5-dichloro-o-quinodimethane (8) as the key step. 6,7-Dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide (15) was found to be an ideal precursor for the generation of the elusive intermediate 8. The ribosylation of 6,7-dichloronaphtho[2,3-d]imidazoles was influenced by the functional group at the 2-position and 6,7-dichloro-2-methylthionaphtho[2,3-d]imidazole (3c) was found to smoothly undergo ribosylation. The 2-methylthio group of the unprotected nucleoside 25 was converted into a chloro group under mild conditions to give nucleoside 2 in high yield.

  DOI：

  10.1021/jo971152o

文献信息

• Nonapeptide and decapeptide agonists of luteinizing hormone releasing hormone containing heterocyclic amino acid residues, methods for their preparation, pharmaceutical compounds containing them, and their pharmaceutical use
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0042753A1

  公开（公告）日：1981-12-30

  Nonapeptide and decapeptide analogs of LH-RH of the formula (pyro)Glu-His-V-Ser-W-X-Y-Arg-Pro-Z (I) and the pharmaceutically acceptable salts thereof wherein: V is tryptophyl, phenylalanyl or 3-(1-naphthyl)-L-alanyl; W is tyrosyl, phenylalanyl or 3-(1-pentafluorophenyl)-L-alanyl; X is a D-amino acid residue of the formula: wherein R is a heterocyclic aryl containing radical selected from radicals represented by the following structural formulas: wherein A and A' are independently selected from hydrogen, lower alkyl, chlorine, and bromine, and G is selected from oxygen, nitrogen, and sulfur; Y is leucyl, isoleucyl, nor-leucyl or N-methyl-leucyl; Z is glycinamide or -NH-R', wherein: R' is lower alkyl, cycloalkyl, fluoro lower alkyl or O II -NH-C-NH-R2 wherein R2 is hydrogen or lower alkyl, are disclosed. These compounds exhibit potent LH-RH agonist properties.

  式中的 LH-RH 的非肽和十肽类似物 (pyro)Glu-His-V-Ser-W-X-Y-Arg-Pro-Z (I)及其药学上可接受的盐类 其中： V 是色氨酰、苯丙氨酰或 3-(1-萘基)-L-丙氨酰； W 是酪氨酰、苯丙氨酰或 3-(1-五氟苯基)-L-丙氨酰； X 是式中的 D-氨基酸残基： 其中 R 是杂环芳基，选自下列结构式所代表的基团： 其中 A 和 A'独立地选自氢、低级烷基、氯和溴，G 选自氧、氮和硫； Y 是亮氨酰，异亮氨酰，非亮氨酰或 N-甲基亮氨酰； Z 是甘氨酰胺或-NH-R'，其中： R' 是低级烷基、环烷基、氟低级烷基或 O II -NH-C-NH-R2 其中 R2 是氢或低级烷基、 公开了这些化合物。这些化合物具有强效的 LH-RH 激动剂特性。
• US4318905A
  申请人：——

  公开号：US4318905A

  公开（公告）日：1982-03-09
• US4792508A
  申请人：——

  公开号：US4792508A

  公开（公告）日：1988-12-20
• Synthesis of 2,6,7-Trichloro-1-(β-<scp>d</scp>-ribofuranosyl)naphtho[2,3-<i>d</i>]imidazole:  A Linear Dimensional Analogue of the Antiviral Agent TCRB
  作者：Zhijian Zhu、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jo971152o

  日期：1998.2.1

  Human cytomegalovirus (HCMV) remains a significant clinical problem in neonates and immunocompromised individuals such as those undergoing transplantation as well as individuals with acquired immune deficiency syndrome (AIDS). Recently in our laboratory, 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB, 1a) and 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BDCRB, 1b) were found to have better activities in cell culture studies against HCMV than the clinically used agents ganciclovir and foscarnet. These benzimidazole compounds appear to act by a unique mechanism. However, as the biological target of TCRB and BDCRB has not been completely identified, 2,6,7-trichloro-1-(beta-D-ribofuranosyl)naphthol[2,3-d]imidazole (2) was designed as a linear dimensional analogue of TCRB for a study on the spatial limitation of the binding site in the target enzyme. In the synthesis, a convenient route was developed for the synthesis of 2-substituted 6,7-dichloronaphtho[2,3-d]imidazoles involving a Diels-Alder reaction of 4,5-dichloro-o-quinodimethane (8) as the key step. 6,7-Dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide (15) was found to be an ideal precursor for the generation of the elusive intermediate 8. The ribosylation of 6,7-dichloronaphtho[2,3-d]imidazoles was influenced by the functional group at the 2-position and 6,7-dichloro-2-methylthionaphtho[2,3-d]imidazole (3c) was found to smoothly undergo ribosylation. The 2-methylthio group of the unprotected nucleoside 25 was converted into a chloro group under mild conditions to give nucleoside 2 in high yield.