1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester | 900189-14-2

分子结构分类

有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物

中文名称

——

中文别名

——

英文名称

1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester

英文别名

methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate；isoquinoline-5,8-quinone；Methyl 1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate；methyl 1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate

1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester化学式

CAS

900189-14-2

化学式

C₁₃H₁₁NO₄

mdl

——

分子量

245.235

InChiKey

OQQVVWOLFDHEGI-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

120-122 °C(Solv: hexane (110-54-3))
沸点：

461.8±45.0 °C(Predicted)
密度：

1.316±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

1
重原子数：

18
可旋转键数：

2
环数：

2.0
sp3杂化的碳原子比例：

0.23
拓扑面积：

73.3
氢给体数：

0
氢受体数：

5

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl 7-amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153595-09-5	C₁₃H₁₂N₂O₄	260.249
——	methyl 6,7-dibromo-5,8-dihydro-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-22-9	C₁₃H₉Br₂NO₄	403.027
——	methyl 6,7-dichloro-5,8-dihydro-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-21-8	C₁₃H₉Cl₂NO₄	314.125
——	methyl 7-(n-butylamino)-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153595-01-7	C₁₇H₂₀N₂O₄	316.357
——	methyl 7-phenylamino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153594-86-5	C₁₉H₁₆N₂O₄	336.347
——	methyl 7-cyclohexylamino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153595-05-1	C₁₉H₂₂N₂O₄	342.395
——	Methyl 7-(4-hydroxyphenyl)sulfanyl-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-19-4	C₁₉H₁₅NO₅S	369.398
——	Methyl 1,3-dimethyl-7-(4-methylphenyl)sulfanyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-18-3	C₂₀H₁₇NO₄S	367.425
——	methyl 7-(4-hydroxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153594-88-7	C₁₉H₁₆N₂O₅	352.346
——	Methyl 1,3-dimethyl-7-(4-methylanilino)-5,8-dioxoisoquinoline-4-carboxylate	1428248-15-0	C₂₀H₁₈N₂O₄	350.374
——	Methyl 7-(4-bromoanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-17-2	C₁₉H₁₅BrN₂O₄	415.243
——	Methyl 7-(4-iodoanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-16-1	C₁₉H₁₅IN₂O₄	462.244
——	methyl 7-(4-fluorophenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153594-93-4	C₁₉H₁₅FN₂O₄	354.338
——	methyl 7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153594-90-1	C₂₀H₁₈N₂O₅	366.373
——	methyl 7-(4-morpholino)-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153595-07-3	C₁₇H₁₈N₂O₅	330.34
——	Methyl 7-(3,4-dimethylphenyl)sulfanyl-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-20-7	C₂₁H₁₉NO₄S	381.452
——	methyl 7-(1-adamantylamino)-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153595-03-9	C₂₃H₂₆N₂O₄	394.47
——	methyl 7-(methylphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153594-97-8	C₂₀H₁₈N₂O₄	350.374
——	methyl 7-(2,5-dimethoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153594-95-6	C₂₁H₂₀N₂O₆	396.4
——	Methyl 6-bromo-7-(4-bromoanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-13-8	C₁₉H₁₄Br₂N₂O₄	494.139
——	Methyl 6-chloro-1,3-dimethyl-7-(4-methylanilino)-5,8-dioxoisoquinoline-4-carboxylate	1428248-01-4	C₂₀H₁₇ClN₂O₄	384.819
——	Methyl 6-bromo-1,3-dimethyl-7-(4-methylanilino)-5,8-dioxoisoquinoline-4-carboxylate	1428248-09-2	C₂₀H₁₇BrN₂O₄	429.27
——	methyl 6-bromo-7-(4-chlorophenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1428248-12-7	C₁₉H₁₄BrClN₂O₄	449.688
——	Methyl 7-(4-bromoanilino)-6-chloro-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-06-9	C₁₉H₁₄BrClN₂O₄	449.688
——	Methyl 6-chloro-7-(4-iodoanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-07-0	C₁₉H₁₄ClIN₂O₄	496.689
——	Methyl 6-chloro-7-(4-chloroanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-05-8	C₁₉H₁₄Cl₂N₂O₄	405.237
——	Methyl 6-bromo-7-(4-fluoroanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-11-6	C₁₉H₁₄BrFN₂O₄	433.234
——	methyl 7-(ethylphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1153594-99-0	C₂₁H₂₀N₂O₄	364.401
——	Methyl 6-chloro-7-(4-fluoroanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-03-6	C₁₉H₁₄ClFN₂O₄	388.783
——	Methyl 6-chloro-7-(4-cyanoanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-04-7	C₂₀H₁₄ClN₃O₄	395.802
——	methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate	1428248-10-5	C₂₀H₁₇BrN₂O₅	445.269
——	Methyl 6-chloro-7-(4-methoxyanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-02-5	C₂₀H₁₇ClN₂O₅	400.818
——	Methyl 6-chloro-7-(3,4-difluoroanilino)-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate	1428248-08-1	C₁₉H₁₃ClF₂N₂O₄	406.773

反应信息

作为反应物：

描述：

1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester 在盐酸、硝酸作用下，反应 0.5h，以50%的产率得到methyl 6,7-dichloro-5,8-dihydro-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate

参考文献：

名称：

Synthesis and antifungal evaluation of 7-arylamino-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylates

摘要：

7-Arylamino-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylates were synthesized and tested for in vitro antifungal activity against two pathogenic strains of fungi. Most of tested compounds showed good antifungal activity. The results suggest that those 5,8-dioxo-5,8-dihydroisoquinolines would be potent antifungal agents. (C) 2013 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.bmcl.2013.01.130
作为产物：

描述：

methyl (E)-3-aminocrotonate 在 manganese(IV) oxide 、 magnesium sulfate 作用下，以二氯甲烷为溶剂，反应 0.83h，生成 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester

参考文献：

名称：

醌的研究。第41部分：含异喹啉的多环醌的合成和细胞毒性。

摘要：

在寻找新的潜在抗癌药物中，已设计并通过高度区域控制的1,3-二甲基-5,8-二氧代-5,8-二氢异喹啉-4-羧酸甲酯与极化1的异环加成反应合成了含异喹啉醌的多环化合物。，3-二烯和噻唑-邻-喹二甲烷。在正常的人类成纤维细胞和四种不同的人类癌细胞系上测试了新的N-杂环醌。与参考药物依托泊苷相比，两种评估化合物显示出显着的体外活性（IC50：0.44-5.9 microM）。

DOI：

10.1016/j.bmc.2006.03.008

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文献信息

Synthesis and antimicrobial evaluation of amino sugar-based naphthoquinones and isoquinoline-5,8-diones and their halogenated compounds

作者：Flaviana R.F. Dias、Juliana S. Novais、Talita A. do Nascimento Santos Devillart、Wanderson Amaral da Silva、Matheus O. Ferreira、Raquel de S. Loureiro、Vinícius R. Campos、Vitor F. Ferreira、Maria C.B.V. de Souza、Helena C. Castro、Anna C. Cunha

DOI：10.1016/j.ejmech.2018.06.050

日期：2018.8

concentration (MBC) values of the most active compounds were equal to MIC classifying them as bactericidal agents against Gram-negative bacteria. Sixteen compounds among eighteen carbohydrate-based naphthoquinones tested showed no hemolytic effects on health human erythrocytes whereas more susceptibility to hemolytic cleavage was observed when using non-glycoconjugate amino compounds. In silico Absorption

抗生素耐药性已成为一个严重的全球性公共卫生问题，近来很少发现抗生素并将其引入临床实践。因此，迫切需要开发具有新的作用机理的抗菌化合物，尤其是能够逃避已知抗性机理的抗菌化合物。在这项工作中，合成了衍生自异喹啉5,8-二酮和1,4-萘醌的两个系列的糖缀合物和非糖缀合物氨基化合物及其卤代衍生物，并评估了它们对革兰氏阳性菌（粪肠球菌ATCC 29212，金黄色葡萄球菌ATCC 25923，表皮葡萄球菌ATCC 12228，模拟葡萄球菌ATCC 27851）和革兰氏阴性细菌（大肠杆菌ATCC 25922，奇异变形杆菌ProCC 15290 ，肺炎克雷伯菌ATCC 4352和铜绿假单胞菌（ATCC 27853）具有临床重要性的菌株。这项研究表明，衍生自卤代萘醌的糖缀合物对革兰氏阴性菌株更具活性，据文献报道，这种菌株导致感染的治疗更加困难。在临床和实验室标准协会的MIC值（CLSI为0.08-256μg/
On-Water Reactivity and Regioselectivity of Quinones in C–N Coupling with Amines: Experimental and Theoretical Study

作者：Maximiliano Martínez-Cifuentes、Graciela Clavijo-Allancan、Carolina Di Vaggio-Conejeros、Boris Weiss-López、Ramiro Araya-Maturana

DOI：10.1071/ch13355

日期：——

A study about the oxidative coupling of some representative carbo- and heterocyclic non-symmetrical quinones with aryl- and alkylamines, was carried out comparing dichloromethane and water as reaction mediums. We found that the on-water reactions gave better or, at worst, the same results as a conventional organic medium like dichloromethane. Descriptors derived from conceptual density functional theory

比较了二氯甲烷和水作为反应介质，对一些代表性的碳和杂环非对称醌与芳基和烷基胺的氧化偶联进行了研究。我们发现，与常规有机介质（如二氯甲烷）相比，水上反应产生的效果更好，或更糟。从概念密度泛函理论和静电性质方法（例如分子静电势）派生的描述符用于解释观察到的化学反应性和区域选择性。此外，在水上条件用于获得24种具有潜在生物活性的新氨基醌。
Isoquinolinequinone<i>N</i>-oxides as anticancer agents effective against drug resistant cell lines

作者：Ryan D. Kruschel、Alyah Buzid、Udaya B. Rao Khandavilli、Simon E. Lawrence、Jeremy D. Glennon、Florence O. McCarthy

DOI：10.1039/c9ob02441g

日期：——

6- and 7-Substituted isoquinolineN-oxides are identified as redox active, adduct forming, anticancer agents and effective against drug resistant cell lines at nanomolar concentrations.

6-和7-取代的异喹啉N-氧化物被鉴定为具有氧化还原活性、形成加合物、抗癌药剂，并且在纳摩尔浓度下对耐药细胞系有效。
Green Synthesis and Electrochemical Properties of Mono- and Dimers Derived from Phenylaminoisoquinolinequinones

作者：Juana Andrea Ibacache、Jaime A. Valderrama、Judith Faúndes、Alex Danimann、Francisco J. Recio、César A. Zúñiga

DOI：10.3390/molecules24234378

日期：——

assisted by ultrasound and CeCl3·7H2O catalysis “in water”. This eco-friendly procedure was successfully extended to the one-pot synthesis of homodimers derived from the 7-phenylaminoisoquinolinequinone pharmacophore. The electrochemical properties of the monomers and dimers were determined by cyclic and square wave voltammetry. The number of electrons transferred during the oxidation process, associated

在寻找具有潜在抗癌活性的新醌类化合物时，报道了新型异二聚体的合成，其中包含通过亚甲基和亚乙基间隔基连接的细胞毒性7-苯基氨基异喹啉醌和2-苯基氨基萘醌药效团。异二聚体由各自的异喹啉和萘醌以及4,4'-二氨基二苯基烯烃制备。通过超声辅助的氧化胺化反应和“水中”CeCl3·7H2O催化，获得目标异二聚体及其相应的单体。这种环保程序已成功扩展到源自 7-苯基氨基异喹啉醌药效团的同型二聚体的一锅合成。通过循环伏安法和方波伏安法测定单体和二聚体的电化学性质。氧化过程中转移的电子数与氧化还原电位 EI1/2 相关，通过受控电位库仑法测定。
Synthesis and antimicrobial evaluation of promising 7-arylamino-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylates and their halogenated amino compounds for treating Gram-negative bacterial infections

作者：Juliana S. Novais、Vinicius R. Campos、Ana Carolina J. A. Silva、Maria C. B. V. de Souza、Vitor F. Ferreira、Vitor G. L. Keller、Matheus O. Ferreira、Flaviana R. F. Dias、Maíra I. Vitorino、Plínio C. Sathler、Marcos V. Santana、Jackson A. L. C. Resende、Helena C. Castro、Anna C. Cunha

DOI：10.1039/c7ra00825b

日期：——

may cause serious infections, such as pneumonia, which can be fatal especially to immunosuppressed individuals. Hospitalized patients are particularly susceptible to antibiotic-resistant infections, which are worsened when caused by resistant Gram-negative pathogens due to there being few therapeutic options available. Thus, this work describes the synthesis and in vitro antimicrobial profile of 7-arylamino-5

病原细菌可能会引起严重的感染，例如肺炎，这可能对致命的免疫系统造成致命影响。住院患者特别容易受到抗生素耐药性感染，当耐药革兰氏阴性病原体引起耐药性感染时，这种情况会恶化，原因是可用的治疗选择很少。因此，这项工作描述了7-芳基氨基-5,8-二氧代-5,8-二氢异喹啉-4-羧酸盐及其卤代氨基醌对革兰氏阳性和革兰氏阴性细菌的合成和体外抗菌特性。有趣的是，这些生物活性物质已显示出对革兰氏阴性致病菌株的有希望的活性。在这些衍生物中，两种非卤代氨基化合物显示出有希望的MIC和MBC值（MIC = MBC = 1-2μgmL -1）对抗两种具有重要临床意义的革兰氏阴性菌株的大肠杆菌ATCC 25922和铜绿假单胞菌ATCC 27853。此外，单溴和二溴氨基醌也可有效防止大肠杆菌的生长（MIC = MBC = 2-4μgmL -1）。该体外血液相容性评价显示低毒性特征在溶血测定中活性aminoquinon