3-methyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione | 858508-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 3-methyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione
• 英文别名: 3-methyl-1,5-dihydro-2H-benzo[b][1,4]diazepine-2,4(3H)-dione；3-methyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione；3-Methyl-1,5-dihydro-benzo[b][1,4]diazepin-2,4-dion；3-Methyl-1,5-dihydro-1,5-benzodiazepine-2,4-dione
• CAS: 858508-63-1
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: RIVLOIIQEAUEFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione 在 劳森试剂 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以98%的产率得到3-Methyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dithione
  参考文献：
  名称：

  1,5-Benzodiazepines XIV. Synthesis of new substituted 9H-bis-[1,2,4]triazolo[4,3-a:3′,4′-d] [1,5]benzodiazepines and relate compounds endowed with in vitro cytotoxic properties

  摘要：

  A series of 11 new 9H-bis-[1,2,4]triazolo[4,3-a:3',4'-d] [1,5]benzodiazepine derivatives 8e-o was synthesized. Ten of these compounds (8e-m,o), along with four analogues (8a-d) (previously synthesized by us) were tested in vitro in order to evaluate their cytotoxic and anti-HIV-1 properties. In this connection other six original compounds, i.e., five 9-substituted compounds prepared starting from the 6,12-diphenylderivative 8c (compounds 10, 11, 12, 13a,b) and the bis-triazolone derivative 14, were synthesized and tested for the same purpose. While none of the 20 compounds tested exhibited any appreciable anti-HIV-1 activity, some of them exhibited interesting cytotoxic properties, the best results being shown by compounds 8c,d,k and 11 (CC(50) range=3-12 microM). Therefore, these four compounds were further evaluated for their antiproliferative activity against a panel of human tumor cell lines; actually, compounds 8d, 8k and 11 showed antiproliferative properties against either or both leukemia- and lymphoma-derived cell lines in the low micromolar range.

  DOI：

  10.1016/j.farmac.2004.12.005
• 作为产物：
  描述：

  ethyl 2-methyl-N-(2-nitrophenyl)malonamate 在 palladium on activated charcoal 氢气 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 20.0~30.0 ℃ 、103.42 kPa 条件下， 反应 8.0h， 生成 3-methyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione
  参考文献：
  名称：

  1,5-Benzodiazepines XIV. Synthesis of new substituted 9H-bis-[1,2,4]triazolo[4,3-a:3′,4′-d] [1,5]benzodiazepines and relate compounds endowed with in vitro cytotoxic properties

  摘要：

  A series of 11 new 9H-bis-[1,2,4]triazolo[4,3-a:3',4'-d] [1,5]benzodiazepine derivatives 8e-o was synthesized. Ten of these compounds (8e-m,o), along with four analogues (8a-d) (previously synthesized by us) were tested in vitro in order to evaluate their cytotoxic and anti-HIV-1 properties. In this connection other six original compounds, i.e., five 9-substituted compounds prepared starting from the 6,12-diphenylderivative 8c (compounds 10, 11, 12, 13a,b) and the bis-triazolone derivative 14, were synthesized and tested for the same purpose. While none of the 20 compounds tested exhibited any appreciable anti-HIV-1 activity, some of them exhibited interesting cytotoxic properties, the best results being shown by compounds 8c,d,k and 11 (CC(50) range=3-12 microM). Therefore, these four compounds were further evaluated for their antiproliferative activity against a panel of human tumor cell lines; actually, compounds 8d, 8k and 11 showed antiproliferative properties against either or both leukemia- and lymphoma-derived cell lines in the low micromolar range.

  DOI：

  10.1016/j.farmac.2004.12.005

文献信息

• One-pot synthesis of bi- and tricyclic heterocyclic compounds using benzotriazole chemistry
  作者：Mohamed Elagawany、Mohamed A. Ibrahim、Siva S. Panda

  DOI：10.1016/j.tetlet.2016.09.070

  日期：2016.11

  Microwave-mediated one-step synthesis of several bi- and tricyclic heterocycles via the intermolecular cyclization of N-acylbisbenzotriazoles with ortho-phenylenediamine in good yield is reported.

  报道了通过微波介导的N-酰基双苯并三唑与邻苯二胺的分子间环化，几个双环和三环杂环的一步合成，收率很高。
• Synthese und pharmokologische Untersuchung offener und cyclischer Äthylendiamide. 1. Mitteilung über heterocyclische Siebenringe
  作者：J. Büchi、A. Aebi、R. Bosshardt、E. Eichenberger

  DOI：10.1002/hlca.19560390339

  日期：——

  Es wurde die Darstellung einiger 1, 4-Diaza-cycloheptan-5,7-dione und N, N′-Di-dialkylacetyl-äthylendiamine sowie ihre Nebenreaktionen beschrieben. Die Siebenring- Struktur der 1,4-Diaza-cycloheptan-5,7-dione wurde bewiesen. Die hergestellten Verbindungen zeigen praktisch keine sedative und analytische Wirkung.

  Es wurde死于Darstellung einiger 1，4-Diaza-cycloheptan-5,7-dione and N，N'-Di-dialkylacetyl-äthylendiaminesone，而Nebenreaktionen beschrieben。Die Siebenring-Struktur der 1,4-Diaza-cycloheptan-5,7-dione wurde bewiesen。死于镇静和分析。
• Nouvelle application des anhydrides N-carboxy aminoacides : synthese des 1,4-benzodiazepine-2,5-diones
  作者：M. Akssira、H. Kasmi、A. Dahdouh、M. Boumzebra

  DOI：10.1016/s0040-4039(00)74168-2

  日期：1992.3

  A new synthetic method for 1,4-benzodiazepine-2,5-dione (BZD) was accomplished by the coupling of amino acid N-carboxy anhydrides (NCAs) with Boc-anthranilic acid, followed by the deprotection of Boc group and by the ring expansion.

  通过将氨基酸N-羧酸酐（NCA）与Boc-邻氨基苯甲酸偶合，然后将Boc基团脱保护并通过Boc脱保护，从而完成了1,4-苯并二氮杂-2,5-二酮（BZD）的新合成方法。环膨胀。
• Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds
  申请人：Thorsett D. Eugene

  公开号：US20070203108A1

  公开（公告）日：2007-08-30

  Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  本发明涉及抑制β-淀粉样肽的释放和/或合成的化合物，因此在治疗阿尔茨海默病方面具有用途。同时，本发明还涉及包含抑制β-淀粉样肽释放和/或合成的化合物的药物组合物，以及使用这些药物组合物预防和治疗阿尔茨海默病的方法。
• Meyer,R.; Lueders, Justus Liebigs Annalen der Chemie, 1918, vol. 415, p. 31,32
  作者：Meyer,R.、Lueders

  DOI：——

  日期：——