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6-(4-氨基苯基)-4,5-二氢-3(2H)-哒嗪酮 | 21282-90-6

分子结构分类

有机化合物 - 苯类化合物 - 苯和取代衍生物

中文名称

6-(4-氨基苯基)-4,5-二氢-3(2H)-哒嗪酮

中文别名

——

英文名称

6-(4-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone

英文别名

6-(4-aminophenyl)-4,5-dihydropyridazin-3(2H)-one；6-(4-aminophenyl)-4,5-dihydropyridazine-3(2H)-one；6-(4-aminophenyl)-2,3,4,5-tetrahydro-3-oxo-pyridazine；6-(4-Aminophenyl)-2,3,4,5-tetrahydropyridazin-3-one；3-(4-aminophenyl)-4,5-dihydro-1H-pyridazin-6-one

CAS

21282-90-6

化学式

C₁₀H₁₁N₃O

mdl

MFCD00266152

分子量

189.217

InChiKey

XMTUHSIIBGFSTQ-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

240-241℃
密度：

1.35

计算性质

辛醇/水分配系数(LogP)：

0.2
重原子数：

14
可旋转键数：

1
环数：

2.0
sp3杂化的碳原子比例：

0.2
拓扑面积：

67.5
氢给体数：

2
氢受体数：

3

SDS

SDS：2745ee2c6de9aab83c05550cb2638b3d

查看

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
——	N-(4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)acetamide	21394-91-2	C₁₂H₁₃N₃O₂	231.254

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	4,5-dihydro-6-(4-hydrazinophenyl)pyridazin-3(2H)-one	129593-83-5	C₁₀H₁₂N₄O	204.231
——	4,5-dihydro-6-[p-(formylamino)phenyl]-3(2H)-pyridazinone	41896-97-3	C₁₁H₁₁N₃O₂	217.227
——	4,5-dihydro-6-<4-isothiocyanatophenyl>-3(2H)-pyridazinone	86798-60-9	C₁₁H₉N₃OS	231.278
——	N-(4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)acetamide	21394-91-2	C₁₂H₁₃N₃O₂	231.254
——	N-<4-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)phenyl>thiourea	87693-29-6	C₁₁H₁₂N₄OS	248.308
——	6-(4-propionylamino-phenyl)-4,5-dihydro-2H-pyridazin-3-one	21282-94-0	C₁₃H₁₅N₃O₂	245.281
——	N-(6-Hydroxyhexyl)-4-(6-oxo-1,4,5,6-tetrahydro-3-pyridazinyl)aniline	122036-26-4	C₁₆H₂₃N₃O₂	289.378
——	(4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)carbohydrazonoyl dicyanide	131741-03-2	C₁₃H₁₀N₆O	266.262
——	N-[4-(6-Oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-butyramide	85234-89-5	C₁₄H₁₇N₃O₂	259.308
——	acetophenone <4-(2,3,4,5-tetrahydro-3-oxo-6-pyridazinyl)phenyl>hydrazone	129593-88-0	C₁₈H₁₈N₄O	306.367
——	6-(p-Chloracetylaminophenyl)-4,5-dihydropyridazon-(3)	39754-32-0	C₁₂H₁₂ClN₃O₂	265.699
——	2-Bromo-N-[4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-acetamide	88555-40-2	C₁₂H₁₂BrN₃O₂	310.15
——	6-[4-(3-chloro-propionylamino)-phenyl]-4,5-dihydro-2H-pyridazin-3-one	69635-64-9	C₁₃H₁₄ClN₃O₂	279.726
司那佐旦	MCI-154	98326-32-0	C₁₅H₁₄N₄O	266.302
——	6-[4-(2,2-dicyanovinyl)aminophenyl]-4,5-dihydropyridazin-3(2H)one	131741-25-8	C₁₄H₁₁N₅O	265.274
——	6-[p-(cyanoacetylamino)-phenyl]-4.5,-dihydro-3(2H)-pyridazinone	88012-36-6	C₁₃H₁₂N₄O₂	256.264
——	2-methyl-6-(4-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone	52241-06-2	C₁₁H₁₃N₃O	203.244
——	Pentanoic acid [4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-amide	85221-79-0	C₁₅H₁₉N₃O₂	273.335
——	6-[4-(4-chloro-butyrylamino)-phenyl]-4,5-dihydro-2H-pyridazin-3-one	69635-72-9	C₁₄H₁₆ClN₃O₂	293.753
——	6-[4-(2-chloro-propionylamino)-phenyl]-4,5-dihydro-2H-pyridazin-3-one	39754-33-1	C₁₃H₁₄ClN₃O₂	279.726
——	N-(2-chloroethyl)-N'-<4-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)phenyl>urea	109890-23-5	C₁₃H₁₅ClN₄O₂	294.741
——	N-isopropyl-glycine 4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-anilide	39754-10-4	C₁₅H₂₀N₄O₂	288.349
——	4,5-dihydro-6-amino>phenyl>-3(2H)-pyridazinone	39754-05-7	C₁₅H₂₀N₄O₂	288.349
——	6-(4-(4-fluorobenzylamino)phenyl)-4,5-dihydropyridazin-3(2H)-one	1187387-06-9	C₁₇H₁₆FN₃O	297.332
——	N-allyl-glycine 4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-anilide	39754-13-7	C₁₅H₁₈N₄O₂	286.334
——	6-{4-[(4-methoxybenzylidene)amino]phenyl}-4,5-dihydropyridazin-3(2H)-one	——	C₁₈H₁₇N₃O₂	307.352
——	6-[4-(1,1-diacetylmethylidenehydrazino)phenyl]-4,5-dihydropyridazin-3(2H)on	131741-09-8	C₁₅H₁₆N₄O₃	300.317
——	2-Chloro-N-[4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-butyramide	85221-81-4	C₁₄H₁₆ClN₃O₂	293.753
——	3-chloro-2,2-dimethyl-N-[4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-propionamide	69635-71-8	C₁₅H₁₈ClN₃O₂	307.78
——	N,N-diethyl-glycine 4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-anilide	39840-57-8	C₁₆H₂₂N₄O₂	302.376
——	6-[4-(2,2-diacetylvinyl)aminophenyl]-4,5-dihydropyridazin-3(2H)one	131741-26-9	C₁₆H₁₇N₃O₃	299.329
——	N-sec-butyl-glycine 4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-anilide	39754-11-5	C₁₆H₂₂N₄O₂	302.376
——	6-[4-(1-(4-Pyridyl)ethylidene)aminophenyl]-4,5-dihydropyridazin-3(2H)one	128995-84-6	C₁₇H₁₆N₄O	292.34
——	4-methoxyacetophenone <4-(2,3,4,5-tetrahydro-3-oxo-6-pyridazinyl)phenyl>hydrazone	129593-89-1	C₁₉H₂₀N₄O₂	336.393
——	6-(4-(2-hydroxybenzylamino)phenyl)-4,5-dihydropyridazin-3(2H)-one	1187387-04-7	C₁₇H₁₇N₃O₂	295.341
——	6-[4-[(4,5-dihydro-2-oxazolyl)amino]phenyl]-4,5-dihydro-3(2H)-pyridazinone	109890-24-6	C₁₃H₁₄N₄O₂	258.28
——	(4-(1-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)carbohydrazonoyl dicyanide	——	C₁₄H₁₂N₆O	280.289
——	2-morpholin-4-yl-N-[4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-acetamide	39754-24-0	C₁₆H₂₀N₄O₃	316.36
——	4,5-Dihydro-6-((4-(3-oxo-1-cyclopentenyl)amino)phenyl)-3(2H)-pyridazinone	125068-41-9	C₁₅H₁₅N₃O₂	269.303
——	4,5-dihydro-6-<4-(1H-pyrrol-1-yl)phenyl>-3(2H)pyridazinone	86798-73-4	C₁₄H₁₃N₃O	239.277
——	4,5-dihydro-6-<4-(4H-1,2,4-triazol-4-yl)phenyl>-3(2H)pyridazinone	86798-72-3	C₁₂H₁₁N₅O	241.252
——	6-(4-(3-methoxy-4-hydroxybenzylamino)phenyl)-4,5-dihydropyridazin-3(2H)-one	1187387-05-8	C₁₈H₁₉N₃O₃	325.367
——	6-[4-(1,1-bis(ethoxycarbonyl)methylidenehydrazino)phenyl]-4,5-dihydropyridazin-3(2H)one	131741-13-4	C₁₇H₂₀N₄O₅	360.37
——	N-<<<4-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)phenyl>amino>thiooxomethyl>benzamide	109890-19-9	C₁₈H₁₆N₄O₂S	352.417
——	6-(4-(3,4,5-trimethoxybenzylamino)phenyl)-4,5-dihydropyridazin-3(2H)-one	1187387-03-6	C₂₀H₂₃N₃O₄	369.42
6-[4-[(2-甲基-3-氧代-1-环戊烯基)氨基]苯基]-4,5-二氢-2H-哒嗪-3-酮	4,5-Dihydro-6-(4-((2-methyl-3-oxo-1-cyclopentenyl)-amino)phenyl)-3(2H)-pyridazinone	125068-43-1	C₁₆H₁₇N₃O₂	283.33
——	3-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]-N-[4-(6-oxo-4,5-dihydro-1H-pyridazin-3-yl)phenyl]propanamide	111794-13-9	C₂₃H₂₈N₄O₅	440.499
——	6-[4-(3-{[2-hydroxy-3-(2-methylphenoxy)propyl]amino}propionamido)phenyl]-4,5-dihydro-3(2H)-pyridazinone	111794-09-3	C₂₃H₂₈N₄O₄	424.5
——	2-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]-N-[4-(6-oxo-4,5-dihydro-1H-pyridazin-3-yl)phenyl]acetamide	111794-00-4	C₂₂H₂₆N₄O₅	426.472
——	3-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-4,5-dihydro-1H-pyridazin-6-one	827303-72-0	C₁₆H₁₇N₃O	267.33
——	2-(2-Hydroxy-3-o-tolyloxy-propylamino)-N-[4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-acetamide	111793-97-6	C₂₂H₂₆N₄O₄	410.473
——	2-[(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]-N-[4-(6-oxo-4,5-dihydro-1H-pyridazin-3-yl)phenyl]acetamide	111794-24-2	C₂₅H₂₆N₄O₄	446.506
——	6-<4-(2,3-dihydro-2-thioxo-1H-imidazol-1-yl)phenyl>-4,5-dihydro-3(2H)-pyridazinone	86798-61-0	C₁₃H₁₂N₄OS	272.33
——	6-(4-(1H-indol-3-ylmethylamino)phenyl)-4,5-dihydropyridazin-3(2H)-one	1187387-07-0	C₁₉H₁₈N₄O	318.378
——	3-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]-N-[4-(6-oxo-4,5-dihydro-1H-pyridazin-3-yl)phenyl]propanamide	111794-17-3	C₂₃H₂₅N₅O₄	435.483
——	2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]-N-[4-(6-oxo-4,5-dihydro-1H-pyridazin-3-yl)phenyl]acetamide	111794-04-8	C₂₂H₂₃N₅O₄	421.456
——	4,5-dihydro-6-<4-<2-(methylthio)-1H-imidazol-1-yl>phenyl>-3(2H)-pyridazinone	86798-62-1	C₁₄H₁₄N₄OS	286.357

反应信息

作为反应物：

描述：

6-(4-氨基苯基)-4,5-二氢-3(2H)-哒嗪酮在盐酸、 sodium nitrite 作用下，以乙醇、水为溶剂，反应 121.75h，生成 2-(2-(4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)hydrazineylidene)-N-propyl-3-(propylimino)butanamide

参考文献：

名称：

新型 4,5-3(2H) 哒嗪酮衍生物的合成及其强心、降压和血小板聚集抑制活性

摘要：

摘要 4,5-二氢-3(2H)哒嗪酮，如 CI-914、CI-930 和匹莫苯，以及四氢吡啶并哒嗪 (endralazine) 和全氢哒嗪并二氮杂 (cilazopril) 已被用作有效的正性肌力药、抗高血压药和血小板聚集抑制剂。因此，目前的工作涉及24个目标化合物的合成；4,5-二氢-3(2H)哒嗪酮以及七个报道的中间体。新化合物的化学结构通过微量分析、红外光谱、1H-NMR光谱分析和质谱分析确定了一些代表性化合物。与地高辛相比，最终化合物和中间体 12a-12d 以及报道的中间体化合物 10 的正性肌力作用是在离体兔心脏上体外测定的。获得的数据显示，有 12 种测试化合物表现出比地高辛更高的有效反应，9 种化合物的作用与地高辛相当，8 种化合物的活性低于地高辛。此外，批准的四种化合物的显着降血压效果优于先前报道的化合物 10。此外，两种化合物诱导了完全的血小板聚集抑制。最后两种化合物也进行了

DOI：

10.1007/s12272-010-2222-x
作为产物：

描述：

3-(4-乙酰基氨基苯甲酰基)丙酸在盐酸、一水合肼作用下，以乙醇为溶剂，反应 6.25h，生成 6-(4-氨基苯基)-4,5-二氢-3(2H)-哒嗪酮

参考文献：

名称：

6-芳基-4,5-二氢-3（2H）-哒嗪酮。一类新的具有血小板聚集抑制和降压活性的化合物。

摘要：

本文报道了6-芳基-4,5-二氢-3（2H）-哒嗪酮衍生物的合成及其药理活性。所述化合物在体外和在离体条件下对人血小板表现出对人血小板的聚集抑制作用，以及对大鼠的降血压作用。发现具有6- [对-[（（氯代烷酰基）氨基]苯基]取代基以及在5-位具有甲基的二氢哒嗪酮具有最强的药理作用。这种类型的化合物在体外的抗聚集活性是乙酰水杨酸的高达16000倍，离体的抗聚集活性高达370倍。降压作用是比较物质二肼苯哒嗪的40倍。

DOI：

10.1021/jm00360a004

点击查看最新优质反应信息

文献信息

Repurposing de novo designed entities reveals phosphodiesterase 3B and cathepsin L modulators

作者：Tiago Rodrigues、Yen-Chu Lin、Markus Hartenfeller、Steffen Renner、Yi Fan Lim、Gisbert Schneider

DOI：10.1039/c5cc01376c

日期：——

Scaffold hopping: a computational algorithm correctly predicted the macromolecular target ofde novogenerated small molecular entities.

脚手架跳跃：一种计算算法正确预测了de novo生成的小分子实体的大分子靶标。
말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체 및 이의 용도

申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY 한국과학기술연구원(319980077518) BRN ▼209-82-03522

公开号：KR20200076655A

公开（公告）日：2020-06-29

본 발명은 말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체(hydrazone derivatives) 및 이의 용도에 관한 것이다.

这项发明涉及末端氨基被芳基或杂芳基取代的新的腙衍生物(hydrazone derivatives)及其用途。
Cardiotonic agents. 2. Synthesis and structure-activity relationships of 4,5-dihydro-6-[4-(H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones: a new class of positive inotropic agents

作者：Ila Sircar、Bradley L. Duell、George Bobowski、James A. Bristol、Dale B. Evans

DOI：10.1021/jm00148a006

日期：1985.10

substituent at the 5-position of 1 (CI-914) produced the most potent compound in this series (11, CI-930). Compound 1 is more potent than amrinone whereas compound 11 is more potent than milrinone. The inotropic effects of 1 and 11 are not mediated via stimulation of beta-adrenergic receptors. Selective inhibition of cardiac phosphodiesterase fraction III represents the principal component of the positive

合成了一系列的4,5-二氢-6- [4-（1H-咪唑-1-基）苯基] -3（2H）-哒嗪酮和相关化合物，并评价其正性肌力活性。该系列的大多数成员产生剂量相关的心肌收缩力增加，这与心率相对较小的升高和全身动脉血压的降低有关。在1的5位上引入甲基取代基（CI-914）产生了该系列中最有效的化合物（11，CI-930）。化合物1比氨力农更有效，而化合物11比米力农更有效。1和11的正性肌力作用不是通过刺激β-肾上腺素受体介导的。心脏磷酸二酯酶组分III的选择性抑制代表1和11的正性肌力作用的主要成分。
TRICYCLIC INHIBITORS OF KINASES

申请人：Tong Yunsong

公开号：US20120220572A1

公开（公告）日：2012-08-30

The present invention relates to compounds of formula (I) or pharmaceutical acceptable salts, wherein X, Y, Z, R 3 and R 4 are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as wee-1 and methods of treating diseases such as cancer.

本发明涉及式(I)的化合物或药用可接受的盐，其中X、Y、Z、R3和R4在描述中有定义。本发明还涉及含有上述化合物的组合物，用于抑制wee-1等激酶，并治疗癌症等疾病的方法。
Design and synthesis of a series of combined vasodilator-.beta.-adrenoceptor antagonists based on 6-arylpyridazinones

作者：R. A. Slater、W. Howson、G. T. G. Swayne、E. M. Taylor、D. R. Reavill

DOI：10.1021/jm00397a013

日期：1988.2

synthesized and evaluated as combined vasodilator/beta-adrenoceptor antagonists and potential antihypertensive agents. Many of the early compounds displayed an unacceptably high level of intrinsic sympathomimetic activity (ISA) and a relatively short duration of action. Disubstitution in the 2,3-positions or in the 4-position of the aryloxy ring gave compounds with low ISA levels and, in some instances,

已经合成了一系列新的6- [4-[[（（芳氧基）酰基]氨基]苯基] -4,5-二氢吡啶并酮，并被评估为血管扩张剂/β-肾上腺素能受体拮抗剂和潜在的降压药。许多早期化合物显示出高水平的固有拟交感神经活性（ISA）和相对较短的作用时间。在芳氧基环的2，3-位或4-位二取代得到的化合物具有较低的ISA水平，并且在某些情况下改善了作用时间。所有这些化合物都是血管扩张药，但5-甲基哒嗪酮衍生物的抗高血压活性始终高于其5-H较低的同系物。