2-acetamido-3-amino-1,4-naphthoquinone | 13755-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetamido-3-amino-1,4-naphthoquinone
• 英文别名: 2-Acetylamino-3-amino-1,4-naphthoquinone；N-(3-amino-1,4-dioxonaphthalen-2-yl)acetamide
• CAS: 13755-96-9
• 化学式: C₁₂H₁₀N₂O₃
• mdl: MFCD02934633
• 分子量: 230.223
• InChiKey: IZJNNHJVNPVRHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  89.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-acetamido-3-amino-1,4-naphthoquinone 在 盐酸 、 sodium dithionite 、 硫酸 、 sodium nitrite 作用下， 反应 41.5h， 生成 6-acetoxy-4,9-dihydro-4,9-dioxo-1H-naphtho[2,3-d]-v-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
• 作为产物：
  描述：

  N-(3-氯-1,4-二氢-1,4-二氧代-2-萘基)乙酰胺 在 氨 作用下， 以 硝基苯 为溶剂， 反应 1.0h， 以92%的产率得到2-acetamido-3-amino-1,4-naphthoquinone
  参考文献：
  名称：

  1,2-二取代萘[2,3-d]咪唑-4,9-二酮及相关化合物的合成及细胞毒性。

  摘要：

  在继续寻找对缓慢生长的实体瘤具有选择性的潜在抗癌药物候选药物的过程中，我们合成了一系列铅结构的1-乙基和2-取代衍生物，即1-乙基-2-甲基萘[2,3-]。 d]咪唑-4，9-二酮（5）。据报道，它们在美国国家癌症研究所的体外癌细胞系中具有细胞毒活性。通常，各种烷基，苯基或苄基部分的取代不会提高活性，并且化合物5仍然是活性最高的萘并[2,3-d]咪唑-4,9-二酮衍生物。但是，发现几种相关的2-（酰基氨基）-3-氯-1,4-萘醌（2f-j）具有较高的活性和选择性。化合物2i，2-[（（2-氟苯基）乙酰胺基] -3-氯-1,4-萘醌，

  DOI：

  10.1021/jm950247k

文献信息

• Synthesis of a new polypyridinic highly conjugated ligand with electron-acceptor properties
  作者：Ramiro Dı́az、Oscar Reyes、Angélica Francois、Ana Marı́a Leiva、Bárbara Loeb

  DOI：10.1016/s0040-4039(01)01289-8

  日期：2001.9

  A new acceptor polypyridinic ligand functionalized with a quinone fragment is reported. The ligand, dipyrido[3,2-a:2′,3′-c]-benzo[3,4]-phenazine-11,16-quinone, Nqphen, was synthesized by condensation of 1,10-phenanthroline-5,6-dione and 2,3-diamino-1,4-naphthoquinone. The syntheses of two rhenium complexes with this ligand are also reported.

  报道了用醌片段官能化的新受体多吡啶配体。配位体二吡啶基[3,2- a：2'，3'- c ]-苯并[3,4]-吩嗪-11,16-醌Nqphen是通过1,10-菲咯啉-5的缩合合成的， 6-二酮和2,3-二氨基-1,4-萘醌。还报道了具有该配体的两种rh配合物的合成。
• Synthesis and Antiplatelet, Antiinflammatory and Antiallergic Activities of 2,3-Disubstituted 1,4-Naphthoquinones.
  作者：Jin-Cherng LIEN、Li-Jiau HUANG、Jih-Pyang WANG、Che-Ming TENG、Kuo-Hsiung LEE、Sheng-Chu KUO

  DOI：10.1248/cpb.44.1181

  日期：——

  Modification of 2-acetamido-3-chloro-1,4-naphthoquinone, which has potent antiplatelet, antiallergic and antiinflammatory activities, led to a series of 2,3-disubstituted 1,4-naphthoquinones. Some of these compounds showed significant antiplatelet, antiallergic and antiinflammatory activities. Among them, 2-methoxy-3-chloro-1,4-naphthoquinone (15) and 2-ethoxy-3-chloro-1,4-naphthoquinone (17) exhibited

  具有有效的抗血小板，抗过敏和抗炎活性的2-乙酰氨基-3-氯-1,4-萘醌的修饰导致了一系列的2,3-二取代的1,4-萘醌。这些化合物中的一些显示出显着的抗血小板，抗过敏和抗炎活性。其中，2-甲氧基-3-氯-1,4-萘醌（15）和2-乙氧基-3-氯-1,4-萘醌（17）对嗜中性粒细胞和肥大细胞脱粒表现出有效的抑制作用。2-甲氧基-1,4-萘醌（20）和2-乙氧基-1,4-萘醌（21）对中性粒细胞超氧化物的形成具有有效的抑制作用。因此，选择了这四种化合物进行进一步评估。
• 2,3,5,6-Tetra-amino-1,4-benzochinon (TABC)
  作者：E. Winkelmann

  DOI：10.1016/s0040-4020(01)82792-7

  日期：1969.1

  Several methods of synthesis of TABC, its properties and significant reactions, are described. The relationship between the mode of reaction and substitution of the TABC is demonstrated by examples and compared with corresponding Diaminonaphthoquinones and related systems.

  描述了TABC的几种合成方法，其性质和重要的反应。通过实施例证明了TABC的反应模式与取代之间的关系，并与相应的二氨基萘醌和相关体系进行了比较。
• Naphthoquinone antitumor compound and method
  申请人：The University of North Carolina at Chapel Hill

  公开号：US06174918B1

  公开（公告）日：2001-01-16

  The invention provides 1,4-naphthoquinone compounds and a method for inhibiting tumor cell growth in a subject by administering such compounds. The compounds are represented by the structures: where R1 is lower alkyl, halogenated lower alkyl, phenyl, benzyl, phenethyl, or —(CH2)mCOOX, where m is 2 or 3 and X is H, methyl, or ethyl; R2 is halo or NHY, where Y is hydrogen, loweralkyl, halogenated lower alkyl, hydroxylated lower alkyl, lower dialkylaminoalkyl, phenyl, benzyl, or phenethyl; R3 is lower alkyl, halogenated lower alkyl, phenyl, benzyl, phenethyl, or —(CH2)mCOOX, where m and X are as defined for R1 above; and R4 is hydrogen, lower alkyl, lower aminoalkyl, halogenated lower alkyl, phenyl, benzyl, or phenethyl.

  本发明提供了1,4-萘醌化合物及通过给予该化合物抑制肿瘤细胞生长的方法。该化合物的结构式为：其中，R1为低碳基、卤代低碳基、苯基、苄基、苯乙基或—(CH2)mCOOX，其中m为2或3，X为H、甲基或乙基；R2为卤或NHY，其中Y为氢、低碳基、卤代低碳基、羟基化低碳基、低二烷基氨基烷基、苯基、苄基或苯乙基；R3为低碳基、卤代低碳基、苯基、苄基、苯乙基或—(CH2)mCOOX，其中m和X如上所述；R4为氢、低碳基、低氨基烷基、卤代低碳基、苯基、苄基或苯乙基。
• 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。