8-hydroxy-5,10-dihydro-11-dioxodibenzo<1,4>diazepine | 76039-66-2

• 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: 8-hydroxy-5,10-dihydro-11-dioxodibenzo<1,4>diazepine
• 英文别名: 3-Hydroxy-5,11-dihydrobenzo[b][1,4]benzodiazepin-6-one
• CAS: 76039-66-2
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: YXHPRISQAFJFFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxy-5,10-dihydro-11-dioxodibenzo<1,4>diazepine 在 氢溴酸 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 异丙醇 、 mineral oil 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Design, Synthesis and Anticancer Activity Evaluation of Diazepinomicin Derivatives

  摘要：

  合成了一系列地西泮米辛衍生物，并在体外评估了其对人类癌瘤细胞系的生长抑制活性。结果表明这种化合物具有抗癌选择性。根据结果，讨论了初步的结构-活性关系。

  DOI：

  10.2174/1570180811310040011
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 盐酸 、 4-二甲氨基吡啶 、 copper(l) iodide 、 硝酸 、 三溴化硼 、 potassium carbonate 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.75h， 生成 8-hydroxy-5,10-dihydro-11-dioxodibenzo<1,4>diazepine
  参考文献：
  名称：

  Design, Synthesis and Anticancer Activity Evaluation of Diazepinomicin Derivatives

  摘要：

  合成了一系列地西泮米辛衍生物，并在体外评估了其对人类癌瘤细胞系的生长抑制活性。结果表明这种化合物具有抗癌选择性。根据结果，讨论了初步的结构-活性关系。

  DOI：

  10.2174/1570180811310040011

文献信息

• Further studies on the cyclisation of 3-hydroxy-2'-nitrodiphenyl ethers and related compounds
  作者：C.W. Bird、M. Latif

  DOI：10.1016/0040-4020(80)80079-2

  日期：1980.1

  been examined as a potential route to 1H-phenoxazinones. Unexpectedly, cyclisation of the dichloro compound proceeded with loss of a Cl and yielded 2-chloro-3H-phenoxazin-3-one. The cyclisation of a range of analogous substrates has been investigated and shown to provide novel and convenient syntheses of 3-amino-phenoxazine, 3H-phenothiazin-3-one and 8-hydroxy-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

  已经研究了3-羟基-2′-硝基二苯基醚的4，6-二甲基和4，6-二氯衍生物的还原环化作为制备1H-苯恶嗪酮的潜在途径。出乎意料的是，二氯化合物的环化在失去Cl的情况下进行并产生了2-氯-3H-苯恶嗪-3-酮。已研究了一系列类似底物的环化作用，并证明它们可提供新颖，方便的合成方法，包括3-氨基-吩恶嗪，3H-吩噻嗪-3-酮和8-羟基-5,10-二氢-11H-二苯并[b， e] [1,4] diazepin-11-one。
• New (Sulfonyloxy)piperazinyldibenzazepines as Potential Atypical Antipsychotics:  Chemistry and Pharmacological Evaluation
  作者：Yi Liao、Bastiaan J. Venhuis、Nienke Rodenhuis、Wia Timmerman、Håkan Wikström、Eddie Meier、Gerd D. Bartoszyk、Henning Böttcher、Christoph A. Seyfried、Staffan Sundell

  DOI：10.1021/jm991005d

  日期：1999.6.1

  A series of 2- or 8-trifluoromethylsulfonyloxy (TfO) and 2- or 8-methylsulfonyloxy (MsO) 11-piperazinyldibenzodiazepines, -oxazepines, and -thiazepines were synthesized and evaluated in pharmacological models for their potential clozapine-like properties. In receptor binding assays, the 2-TfO analogues (18a, GMC2-83; 24, GMC3-06; and previously reported GMC1-169, 9a) of the dibenzazepines have profiles

  合成了一系列的2-或8-三氟甲基磺酰氧基（TfO）和2-或8-甲基磺酰氧基（MsO）11-哌嗪基二苯并二氮杂卓，-氧杂ze庚因和-噻氮pine，并在药理模型中评估了它们潜在的类氯氮平性质。在受体结合试验中，二苯并ze庚因的2-TfO类似物（18a，GMC2-83； 24，GMC3-06；先前报道的GMC1-169，9a）具有与氯氮平相当的特性，可作用于多种CNS受体除了它们缺乏M1受体亲和力。将2-TfO引入氯氮平可导致化合物9e（GMC61-39）具有与氯氮平相似的结合特性，包括具有M1受体亲和力。有趣的是，MsO类似物以及8-TfO类似物不具有或具有弱的多巴胺能和血清素能亲和力，但是所有8-磺酰氧基类似物的确具有M1亲和力。在进行的行为研究中表明了潜在的抗精神病功效和诱导EPS的倾向，2-TfO类似物以剂量依赖性方式有效阻断了阿扑吗啡诱导的小鼠爬升，ED50值（mg / kg）为2.1
• BIRD C. W.; LATIF M., TETRAHEDRON, 1980, 36, NO 12, 1813-1816
  作者：BIRD C. W.、 LATIF M.

  DOI：——

  日期：——
• Synthesis and Pharmacological Evaluation of Triflate-Substituted Analogues of Clozapine:  Identification of a Novel Atypical Neuroleptic
  作者：Yi Liao、Peter DeBoer、Eddie Meier、Håkan Wikström

  DOI：10.1021/jm9704457

  日期：1997.12.1

  The trifluoromethanesulonyloxy (TfO) analogues 3 and 4 of 8-chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo[b,e][1,4]diazepine (clozapine, 1) and its 2-chloro isomer (iso-clozapine, 2), respectively, were synthesized via their OMe and OH analogues with the conventional synthetic method of the tricyclic dibenzodiazepines and evaluated pharmacologically along with their parent drugs. The binding profile of the 2-OTf analogue (4) is comparable to the binding profile of 1, although the affinity for the dopamine (DA) D-2 receptors is higher (IC50 values are 31 nM and 330 nM for compounds 4 and 1, respectively). Interestingly, no notable affinity for muscarinic receptors could be detected in compound 4. On the contrary, the 3-OTf analogue 3 only displayed affinity for muscarinic M-1 receptors (IC50 value 35 nM) and no affinity (IC50 value > 500 nM) for the other receptors tested. The 10 mu mol/kg sc dose, but nod the 10 mu mol/kg po dose, of compound 4 stimulated the output of DA, Increases of 80% and 35% in DOPAC output from the dorsal striatum were seen after sc and po administrations of 10 mu mol/kg of compound 4, respectively. Doses up to 100 mu mol/kg of compound 3 had no effect on either parameter. Doses up to 100 mu mol/kg of compound 4 were not cataleptogenic, but significantly decreased apomorphine-induced locomotor activity. In conclusion, compound 4 (GMC1-169) is a new clozapine-like neuroleptic candidate, which is lacking anticholinergic properties and displays a higher potency, as compared to clozapine (1) itself.
• Design, Synthesis and Anticancer Activity Evaluation of Diazepinomicin Derivatives
  作者：Yongguo Yu、Jianbo Wu、Fan Lei、Lei Chen、Weili Wan、Li Hai、Mei Guan、Yong Wu

  DOI：10.2174/1570180811310040011

  日期：2013.3.1

  A series of diazepinomicin derivatives were synthesized and evaluated in vitro for their growth inhibitory activity against the human carcinoma cell lines. The results indicated the anticancer selectivity of this kind of compounds. Based on the results, preliminary structure-activity relationships were discussed.

  合成了一系列地西泮米辛衍生物，并在体外评估了其对人类癌瘤细胞系的生长抑制活性。结果表明这种化合物具有抗癌选择性。根据结果，讨论了初步的结构-活性关系。