4,9-dihydro-6,7-dimethyl-5-nitro-4,9-dioxo-1H-naphtho-[2,3-d]-triazole | 72364-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,9-dihydro-6,7-dimethyl-5-nitro-4,9-dioxo-1H-naphtho-[2,3-d]-triazole
• 英文别名: 4,9-Dihydro-6,7-dimethyl-4,9-dioxo-5-nitronaphtho[2,3-d]-triazole；6,7-dimethyl-5-nitro-2H-benzo[f]benzotriazole-4,9-dione
• CAS: 72364-98-8
• 化学式: C₁₂H₈N₄O₄
• 分子量: 272.22
• InChiKey: JIOKGODKMVWGKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-dibromo-6,7-dimethylnaphthalene-1,4-dione 在 盐酸 、 sodium dithionite 、 硫酸 、 氨 、 硝酸 、 sodium nitrite 作用下， 以 硝基苯 为溶剂， 反应 2.92h， 生成 4,9-dihydro-6,7-dimethyl-5-nitro-4,9-dioxo-1H-naphtho-[2,3-d]-triazole
  参考文献：
  名称：

  Studies on v-triazoles. 9. Antiallergic 4,9-dihydro-4,9-dioxo-1H-naphtho[2,3-d]-v-triazoles

  摘要：

  A short series of the title compounds was prepared and evaluated for antiallergic activity in the rat passive cutaneous anaphylaxis screen. All but the two N-methylated derivatives were active in this screen by the intravenous route, the most potent being the symmetrical dimethyl compound, 4,9-dihydro-6,7-dimethyl-4,9-dioxo-1H-naphtho[2,3-d]-v-triazole, and its 5-nitro derivative. The latter two compounds were noticeably more potent than disodium cromoglycate, and one of these, the unnitrated material, was selected for further evaluation as a potential antiasthmatic drug.

  DOI：

  10.1021/jm00359a016

文献信息

• 4,9-Dihydro-4,9-dioxo-1H-naphtho(2,3-d) triazoles, their preparation and antiallergic compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0002310A1

  公开（公告）日：1979-06-13

  Compounds of formula (I): and pharmaceutically acceptable salts thereof wherein R1, R2, R3 and R4 which may be the same or different, represent hydrogen, halogen, nitro, lower alkyl, or lower alkoxy, or any adjacent two of R1 to R4 taken together represent an alkylene group containing from 3 to 5 carbon atoms or a 1,4-buta-1,3- dienylene group are disclosed together with a method for their preparation. The compounds are useful as anti-allergic agents. With the exception of 4,9-dioxo-1H-naphtho-[2,3-d]-triazole, and its salts, all compounds of formula (I) are novel.

  式（I）化合物：及其药学上可接受的盐，其中 R1、R2、R3 和 R4 可以相同或不同，代表氢、卤素、硝基、低级烷基或低级烷氧基，或 R1 至 R4 中任意相邻两个共同代表含有 3 至 5 个碳原子的亚烷基或 1,4-丁-1,3-二烯基。 这些化合物可用作抗过敏剂。 除 4,9-二氧代-1H-萘并-[2,3-d]-三唑及其盐类外，所有式（I）化合物均为新型化合物。
• Process for preparing therapeutically active triazoles
  申请人：BEECHAM GROUP PLC

  公开号：EP0033214A2

  公开（公告）日：1981-08-05

  Process for the preparation of compounds of the formula (I): and pharmaceutically acceptable salts thereof wherein R1, R2, R3 and R4 which may be the same or different, represent hydrogen, halogen, nitro, lower alkyl or lower alkoxy, where lower means of up to six carbon atoms, or any adjacent two of R1 to R4 taken together represent an alkylene group containing from 3 to 5 carbon atoms or a 1,4-buta-1,3- dienylene group, by removal of CH2R5 wherein R5 is phenyl optionally substituted with one or two groups selected from C1-4 alkyl, C1-4 alkoxy, halogen or nitro from a compound of formula (II): with an alkali metal C1-4 primary alkoxide.

  制备式(I)化合物的工艺： 及其药学上可接受的盐 其中 R1、R2、R3 和 R4 可以相同或不同，代表氢、卤素、硝基、低级烷基或低级烷氧基，其中低级烷基是指最多 6 个碳原子的烷基，或 R1 至 R4 中任意相邻的两个共同代表含有 3 至 5 个碳原子的亚烷基或 1,4-丁-1,3-二烯基： 与碱金属 C1-4 伯烷氧基。
• Process for preparing anti-allergy naphthotriazoles
  申请人：BEECHAM GROUP PLC

  公开号：EP0033215A2

  公开（公告）日：1981-08-05

  Process for the preparation of compounds of the formula (I): and pharmaceutically acceptable salts thereof wherein R1, R2, R3 and R4 which may be the same or different, represent hydrogen, halogen, nitro, lower alkyl or lower alkoxy, where lower means of up to six carbon atoms, or any adjacent two of R1 to R4 taken together represent an alkylene group containing from 3 to 5 carbon atoms or a 1,4-buta-1,3-dienylene group, by removing an N-protecting group Q from a compound of formula (II):

  制备式(I)化合物的工艺： 及其药学上可接受的盐 其中 R1、R2、R3 和 R4 可以相同或不同，代表氢、卤素、硝基、低级烷基或低级烷氧基，其中低级烷基是指最多六个碳原子的烷基，或 R1 至 R4 中任意相邻的两个共同代表含有 3 至 5 个碳原子的亚烷基或 1,4-丁-1,3-二烯基：
• BUCKLE, D. R.;SMITH, H.;SPICER, B. A.;TEDDER, J. M., J. MED. CHEM., 1983, 26, N 5, 714-719
  作者：BUCKLE, D. R.、SMITH, H.、SPICER, B. A.、TEDDER, J. M.

  DOI：——

  日期：——
• US4263309A
  申请人：——

  公开号：US4263309A

  公开（公告）日：1981-04-21