8,9-Dimethoxy-6-(3-nitrophenyl)-2,11-dihydro-[1,2,4]triazolo[4,3-c][2,3]benzodiazepin-3-one | 320350-03-6

分子结构分类

有机化合物 - 有机杂环化合物 - 三唑并二氮卓类

中文名称

——

中文别名

——

英文名称

8,9-Dimethoxy-6-(3-nitrophenyl)-2,11-dihydro-[1,2,4]triazolo[4,3-c][2,3]benzodiazepin-3-one

英文别名

——

8,9-Dimethoxy-6-(3-nitrophenyl)-2,11-dihydro-[1,2,4]triazolo[4,3-c][2,3]benzodiazepin-3-one化学式

CAS

320350-03-6

化学式

C₁₈H₁₅N₅O₅

mdl

——

分子量

381.348

InChiKey

PLRBYKVLIWSBMJ-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

2.2
重原子数：

28
可旋转键数：

3
环数：

4.0
sp3杂化的碳原子比例：

0.17
拓扑面积：

121
氢给体数：

1
氢受体数：

7

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	7,8-Dimethoxy-1-(3-nitrophenyl)-3,5-dihydro-2,3-benzodiazepine-4-thione	213385-75-2	C₁₇H₁₅N₃O₄S	357.39
——	7,8-Dimethoxy-1-(3-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4-one	187940-14-3	C₁₇H₁₅N₃O₅	341.323

反应信息

作为反应物：

描述：

8,9-Dimethoxy-6-(3-nitrophenyl)-2,11-dihydro-[1,2,4]triazolo[4,3-c][2,3]benzodiazepin-3-one 在 tin(ll) chloride 作用下，以乙醇为溶剂，反应 1.5h，以65.3%的产率得到6-(3-Aminophenyl)-8,9-dimethoxy-2,11-dihydro-[1,2,4]triazolo[4,3-c][2,3]benzodiazepin-3-one

参考文献：

名称：

11H- [1,2,4]三唑并[4,5-c] [2,3]苯并二氮杂-3（2H）-ones的合成及药理和药代动力学性质的评估。

摘要：

先前已将一系列2，3-苯并二氮杂pine衍生物描述为非竞争性AMPA型谷氨酸受体拮抗剂，可用于治疗癫痫。为了进一步探索AMPA拮抗剂的构效关系，合成了一系列11H- [1,2,4]三唑并[4,5-c] [2,3]苯并二氮杂-3（2H）-（6）从相应的双环1-芳基-3，5-二氢-7，8-二甲氧基-4H-2，3-苯并二氮杂-4--4-酮（2，CFM）开始。发现新化合物具有抗惊厥作用，可对抗DBA / 2小鼠的听觉刺激和瑞士小鼠中的戊四唑或最大电击诱发的癫痫发作。另外，它们拮抗AMPA诱导的癫痫发作，并且其抗惊厥活性通过用阿尼西坦预处理而逆转，因此暗示了AMPA受体的参与。药理研究表明，本文报道的11H- [1,2,4]三唑并[4,5-c] [2,3]苯并二氮杂-3-（2H）-ones（6）显示出与它们的双环类似的抗惊厥活性前体。此外，HPLC研究表明，这些三环衍生物6在体内被转化为相应的2，这

DOI：

10.1021/jm001012y
作为产物：

描述：

7,8-Dimethoxy-1-(3-nitrophenyl)-3,5-dihydro-2,3-benzodiazepin-4-one 在劳森试剂作用下，以甲苯、正丁醇为溶剂，生成 8,9-Dimethoxy-6-(3-nitrophenyl)-2,11-dihydro-[1,2,4]triazolo[4,3-c][2,3]benzodiazepin-3-one

参考文献：

名称：

Design and development of 2,3-benzodiazepine (CFM) noncompetitive AMPA receptor antagonists

摘要：

2,3-Benzodiazepines represent a class of heterocyclic compounds that interact with AMPA-type glutamate receptors in a noncompetitive manner. These compounds have attracted great interest for their pharmacological effects against acute and chronic neurodegenerative diseases, such as ischemia and epilepsy. We synthesized a large number of 2,3-benzodiazepine derivatives, which showed anticonvulsant properties in different seizure models and a noncompetitive blockade of AMPA receptor. This article will briefly mention our work in this field and the main SAR considerations. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

DOI：

10.1016/s0014-827x(01)01186-7

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文献信息

Synthesis and Evaluation of Pharmacological and Pharmacokinetic Properties of 11H-[1,2,4]Triazolo[4,5-c][2,3]benzodiazepin-3(2H)-ones

作者：Maria Zappalà、Rosaria Gitto、Francesca Bevacqua、Silvana Quartarone、Alba Chimirri、Milena Rizzo、Giovambattista De Sarro、Angela De Sarro

DOI：10.1021/jm001012y

日期：2000.12.1

A series of 2,3-benzodiazepine derivatives has been previously described as noncompetitive AMPA-type glutamate receptor antagonists potentially useful for treatment of epilepsy. To further explore the structure-activity relationships of AMPA antagonists, a series of 11H-[1,2,4]triazolo[4,5-c][2,3]benzodiazepin-3(2H)-ones (6) was synthesized starting from the corresponding bicyclic 1-aryl-3, 5-dihydro-7

先前已将一系列2，3-苯并二氮杂pine衍生物描述为非竞争性AMPA型谷氨酸受体拮抗剂，可用于治疗癫痫。为了进一步探索AMPA拮抗剂的构效关系，合成了一系列11H- [1,2,4]三唑并[4,5-c] [2,3]苯并二氮杂-3（2H）-（6）从相应的双环1-芳基-3，5-二氢-7，8-二甲氧基-4H-2，3-苯并二氮杂-4--4-酮（2，CFM）开始。发现新化合物具有抗惊厥作用，可对抗DBA / 2小鼠的听觉刺激和瑞士小鼠中的戊四唑或最大电击诱发的癫痫发作。另外，它们拮抗AMPA诱导的癫痫发作，并且其抗惊厥活性通过用阿尼西坦预处理而逆转，因此暗示了AMPA受体的参与。药理研究表明，本文报道的11H- [1,2,4]三唑并[4,5-c] [2,3]苯并二氮杂-3-（2H）-ones（6）显示出与它们的双环类似的抗惊厥活性前体。此外，HPLC研究表明，这些三环衍生物6在体内被转化为相应的2，这
Design and development of 2,3-benzodiazepine (CFM) noncompetitive AMPA receptor antagonists

作者：Rosaria Gitto、Maria Zappalà、Giovambattista De Sarro、Alba Chimirri

DOI：10.1016/s0014-827x(01)01186-7

日期：2002.2

2,3-Benzodiazepines represent a class of heterocyclic compounds that interact with AMPA-type glutamate receptors in a noncompetitive manner. These compounds have attracted great interest for their pharmacological effects against acute and chronic neurodegenerative diseases, such as ischemia and epilepsy. We synthesized a large number of 2,3-benzodiazepine derivatives, which showed anticonvulsant properties in different seizure models and a noncompetitive blockade of AMPA receptor. This article will briefly mention our work in this field and the main SAR considerations. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

同类化合物

叔-丁基3-(羟甲基)-7,8-二氢-4H-[1,2,3]三唑并[1,5-A][1,4]二氮杂卓-5(6H)-甲酸基酯乙基4-(4H-[1,2,4]三唑并[4,3-a][1,5]苯并二氮卓-5-基)哌嗪-1-羧酸酯 9H-[1,2,4]三唑并[4,3-a][1,4]二氮杂卓 9-氯-5,6-二氢-4-甲基-1-(2-噻吩基)-4H-[1,2,4]三唑并[4,3-a][1,5]苯并二氮杂卓 9-氯-1-(2-呋喃基)-5,6-二氢-4-甲基-4H-[1,2,4]三唑并[4,3-a][1,5]苯并二氮杂卓 8-氯-5-(4-甲基哌嗪-1-基)-6-苯基-[1,2,4]三唑并[4,3-a][1,5]苯并二氮杂卓 8-氯-1-甲基-5-(甲基硫烷基)-6-苯基-6H-[1,2,4]三唑并[4,3-a][1,5]苯并二氮卓 2-[(8-氯-6-苯基-6H-[1,2,4]三唑并[4,3-a][1,5]苯并二氮卓-5-基)硫烷基]-N,N-二甲基乙胺 2-[(8-氯-1-甲基-6-苯基-[1,2,4]三唑并[4,3-a][1,5]苯并二氮杂卓-5-基)硫基]-N,N-二甲基乙胺 1H-环丙并[d][1,2,4]三唑并[4,3-b]哒嗪 1H,5H-[1,2,4]三唑并[1,2-a][1,2]二氮杂卓-1,3,5(2H)-三酮,6,9-二氢-2,7-二甲基-9-(2-吡啶基)- (9ci)-1H-1,2,4-噻唑并[4,3-c][1,3]二氮杂卓 (9ci)-1H-1,2,4-噻唑并[4,3-a][1,4]二氮杂卓 ethyl 1,5-di(4-chlorophenyl)-4a-methyl-3a-phenyl-3a,4a,8,13-tetrahydro-4H-[1,2,4]oxadiazolo[5,4-d][1,2,4]triazolo[4,3-a][1,5]benzodiazepine-7-carboxylate ethyl 1-(4-chlorophenyl)-4a-methyl-5-(4-nitrophenyl)-3a-phenyl-3a,4a,8,13-tetrahydro-4H-[1,2,4]oxadiazolo[5,4-d][1,2,4]triazolo[4,3-a][1,5]benzodiazepine-7-carboxylate ethyl 3,7-di(4-chlorophenyl)-3a-methyl-4a,5-diphenyl-3a,4a,8,13-tetrahydro-4H-bis-[1,2,4-triazolo][4,3-a:3',4'-d][1,5]benzodiazepine-1-carboxylate ethyl 7-(4-chlorophenyl)-3a-methyl-3-(4-nitrophenyl)-4a,5-diphenyl-3a,4a,8,13-tetrahydro-4H-bis-[1,2,4-triazolo][4,3-a:3',4'-d][1,5]benzodiazepine-1-carboxylate 5,6-Dihydro-6-(4-nitrobenzoyl)-4H-[1,2,4]triazolo-[4,3-a][1,5]benzodiazepin 6,7-dibromo-9-[(diethylamino)acetyl]-3H-pyrido[3,2-c]-s-triazolo-[4,3-a][1,5]benzodiazepin-3-one 3-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine 1-ethoxycarbonyl-3a-methyl-3-(4-tolyl)-5-phenyl-3,3a,4,11-tetrahydro-<1,2,4>triazolo<4,3-a><1,5> benzodiazepine aminomethyl-7,8-dihydro-4H-[1,2,3]triazolo[1,5-a][1,4]diazepine-5(6H)-carboxylic acid tert-butyl ester ethyl 3a-methyl-3-(4-nitrophenyl)-4a,5-diphenyl-7-(4-tolyl)-3a,4a,8,13-tetrahydro-4H-bis-[1,2,4-triazolo][4,3-a:3',4'-d][1,5]benzodiazepine-1-carboxylate diethyl trans-3a-methyl-4a-phenyl-3,5-bis(p-nitrophenyl)-3a,4,4a,5-tetrahydro-3H-bis<1,2,4>triazolo<4,3-a:3',4'-d><1,5>benzodiazepine-1,7-dicarboxylate diethyl cis-3a-methyl-4a-phenyl-3,5-bis(p-nitrophenyl)-3a,4,4a,5-tetrahydro-3H-bis<1,2,4>triazolo<4,3-a:3',4'-d><1,5>benzodiazepine-1,7-dicarboxylate ethyl 3-(4-chlorophenyl)-3a-methyl-4a,5-diphenyl-7-(4-tolyl)-3a,4a,8,13-tetrahydro-4H-bis-[1,2,4-triazolo][4,3-a:3',4'-d][1,5]benzodiazepine-1-carboxylate 1-ethoxycarbonyl-3a-methyl-3,5-diphenyl-3,3a,4,11-tetrahydro-<1,2,4>triazolo<4,3-a><1,5> benzodiazepine 4-hydro-5-phenyl-1H-s-triazolo<4,3-a><1,5>benzodiazepin-1-one 2,4-dihydro-5-phenyl-1H-s-triazolo<4,3-a><1,5>benzodiazepin-1-one 4-hydro-2-methyl-5-phenyl-1H-s-triazolo<4,3-a><1,5>benzodiazepin-1-one Dimethyl-1,7 ditriazolo<4,3-a;3,4-d>benzodiazepine-1,5 1-Methyl-5-piperidin-1-yl-4H-2,3,6,10b-tetraaza-benzo[e]azulene 1-Methyl-5-(4-methyl-piperazin-1-yl)-4H-2,3,6,10b-tetraaza-benzo[e]azulene 4-(1-Methyl-4H-2,3,6,10b-tetraaza-benzo[e]azulen-5-yl)-piperazine-1-carboxylic acid ethyl ester 8-Chloro-5-oxo-5,6-dihydro-4H-1,2,6,10b-tetraaza-benzo[e]azulene-3-carboxylic acid ethyl ester (1S,2R,8S,9R)-5-methyl-3,5,7-triazatetracyclo[7.2.1.02,8.03,7]dodec-10-ene-4,6-dione (1S,2S,8R,9R)-5-methyl-3,5,7-triazatetracyclo[7.2.1.02,8.03,7]dodec-10-ene-4,6-dione N,N-diethyl-4H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepin-5-amine 9H-bis<1,2,4>triazolo<4,3-a:3',4'-d><1,5>benzodiazepine N,N-dimethyl-4H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepin-5-amine 4H-<1,2,4>-triazolo<4,3-a><1,5>benzodiazepin-5(6H)-one 1-cyclohexyl-5,6-dihydro-4-(1H-indazol-3-ylmethyl)-5-oxo-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine-6-acetic acid N,N-Dipropyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-amine 1,4-Dimethyl-5,6-dihydro-4H-2,3,6,10b-tetraaza-benzo[e]azulene 2-methyl-hexahydro-6-oxa-2,3a,7c-triaza-4,4e-cyclo-cyclopenta[1,3]cyclopropa[1,2-a]cyclopropa[cd]-as-indacene-1,3-dione r-10a,t-11a-dimethyl-5,6,10,10a,11,11a-hexahydro-1,3,8,10-tetraphenyl-1H-bis<1,2,4>triazolo<4,3-d:3',4'-g><1,4>diazepine 4-(2-Dimethylaminoethyl)-1-methyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a] [1,5]benzodiazepin-5-one 3a,5,5-Trimethyl-1,3-diphenyl-3a,4,5,6-tetrahydro-3H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepine (R)-8-bromo-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine 9-chloro-4-methyl-1-naphthalen-2-yl-5,6-dihydro-4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine