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1.
Mostafa M. Ghorab Marwa G. El-Gazzar Mansour S. Alsaid 《International journal of molecular sciences》2014,15(5):7539-7553
4-Aminoantipyrine was utilized as key intermediate for the synthesis of pyrazolone derivatives bearing biologically active moieties. The newly synthesized compounds were characterized by IR, 1H- and 13C-NMR spectral and microanalytical studies. The compounds were screened as anticancer agents against a human tumor breast cancer cell line MCF7, and the results showed that (Z)-4-((3-amino-5-imino-1-phenyl-1H-pyrazol-4(5H)-ylidene)methylamino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one 5, 3-(4-bromophenyl) -1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 13, 1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1-Hpyrazol- 4-yl)-3-(4-iodophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 14, 3,3′-(4,4′-sulfonylbis(4,1-phenylene))bis(1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol- 4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile) 16, (Z)-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-hydrazono-4-oxo-3-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 17, (Z)-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-oxo-3-phenyl-2-(2-phenylhydrazono)-1,2,3,4-tetrahydro pyrimidine-5-carbonitrile 18, and (Z)-4-(3-amino-6-hydrazono-7-phenyl-6,7-dihydro pyrazolo[3,4-d]pyrimidin-5-yl)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one 19 were the most active compounds with IC50 values ranging from 30.68 to 60.72 μM compared with Doxorubicin as positive control with the IC50 value 71.8 μM. 相似文献
2.
In presence of ammonia/ammonium acetate the 3,5-dimethyl-2-phenyl-1,1-dioxo-1,2-thiazine-4-carbaldehyde ( 1 ) reacts with ethyl cyanoacetate to the ethyl 2-cyano-4-[1-methyl-2-methylthio-2-(N-phenylsulfamoyl)vinyl)-hexa-2,4-dienoate] ( 3 ) and the Knoevenagel condensation product 4-(2-ethoxycarbonyl-2-cyanovinyl)-3,5-dimethyl-6-methylthio-1,1-dioxo-2-phenyl-2H-1,2-thiazine ( 2 a). The 4-(2,2-dicyanovinyl)-3,5-dimethyl-6-methylthio-1,1-dioxo-2-phenyl-2H-1,2-thiazine ( 2b ) is obtained from 1 and malononitril. The masked 1,5-dicarbonyl compound 2a undergoes ring transformation to the 3-cyano-1,6-dimethyl-5-[1-methylthio-2-(N-phenylsulfamoyl)vinyl]pyridin-2-one ( 5 ) with methylamine. With ethanolic ethoxide the condensation products 2a,b afford the 7-amino-6-ethoxycarbonyl-4-methylthio-2,2-dioxo-1-phenyl-benzo[c]1,2-thiazine ( 6a ), respectively the corresponding 6-cyano derivative 6b , while 3 cyclizises to furnish ethyl 2-amino-6-methyl-5-[1-methyl-2-methylthio-2-(N-phenyl-sulfamoyl)vinyl]nicotinate ( 4 ). 相似文献
3.
4.
Farag M. A. Altalbawy 《International journal of molecular sciences》2013,14(2):2967-2979
The title compounds were prepared by reaction of 1,1′-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)diethanone (1) with different aromatic aldehydes 2a–c, namely Furfural (2a), 4-chlorobenzaldehyde (2b) and 4-methoxybenzaldhyde (2c) to yield the corresponding α,β-unsaturated ketones 3a–c. Compound 3 was reacted with malononitrile, 2-cyanoacetamide or 2-cyanothioacetamide yielded the corresponding bis[2-amino-6-(aryl)nicotinonitrile] 4a–c, bis[6-(2-aryl)-2-oxo-1,2-dihydropyridine-3-carbonitrile] 5a–c or bis[6-(2-aryl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile] 6a,b, respectively. The reaction of compound 6a with each of 2-chloro-N-(4-bromophenyl) acetamide (7a), chloroacetamide (7b) in ethanolic sodium ethoxide solution at room temperature to give the corresponding 4,4′-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis-6-(2-furyl)thieno[2,3-b]pyridine-2-carboxamide] derivatives 9a,b. While compound 6a reacted with hydrazine hydrate yielded the 4,4′-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis[6-(2-furyl)-1H-pyrazolo[3,4-b]pyridin-3-amine] 11. The structures of the products were elucidated based on their spectral properties, elemental analyses and, wherever possible, by alternate synthesis. Antimicrobial evaluation of the products was carried out. 相似文献
5.
Tarik E. Ali Mohamed A. Assiri Somaia M. Abdel-Kariem Ibrahim S. Yahia 《Journal of Sulfur Chemistry》2018,39(5):472-482
A number of 6-methyl-5-phenyl-2-sulfido-1,2,3,5-tetrahydro-4H[1,2]oxazolo[4′,5′: 5,6]pyrano[2,3-d][1,3,2]diazaphosphinines 4–11 were synthesized via an interaction of tetraphosphorus decasulfide and Lawesson’s reagent under different conditions with 6-amino-3-methyl-4-phenyl-4H-pyrano[3,2-d][1,2]oxazole-5-carbonitrile (3). The reaction mechanisms for these products were discussed. Structures of the newly synthesized products were established on the basis of elemental analysis and spectral data. 相似文献
6.
K. Gewald S. Rennert R. Schindler H. Schfer 《Advanced Synthesis \u0026amp; Catalysis》1995,337(1):472-477
Amino-thieno[2,3–c]pyrazoles and Amino-thieno[2,3–b]pyrroles The synthesis of thieno[2,3–c]pyrazoles and thieno[2,3–b]pyrroles is described. From the dithioliumsalt ( 1 ) and potassium hydroxide the potassium-(2,2-dicyan-1-methylthio-ethen-1-yl)-thiolate ( 2 ) is formed. This reacts with hydrazine hydrate to form the 3-amino-5-thioxo-pyrazol-4-carbonitrile ( 3 ) S-Alkylation with α-chlorocarbonyl compounds yielding ( 6a–c ) leads via Thorpe-Ziegler-cyclization to 3,4-diamino-thieno[2,3–c]pyrazoles ( 9 ) if the position 1 is alkylated ( 8 ). Acetyl acetone yields 2-mercapto-pyrazolo[1,5–a]pyrimidine ( 5 ). After S-alkylation ( 10a–d ) are immediately cyclized to thieno [2′,3′:3,4]pyrazolo[1,5-a]pyrimidine ( 11a–d ). The ketone ( 6a ) can be cyclized to the pyrazolo [5,1–b]thiazole ( 12 ). 3 reacts with oxalyl chloride to form the 2,3-dioxo-6-thioxo-imidazo[1,2-b]pyrazole ( 13 ) of which S-phenacyl derivative ( 14 ) because the NH-proton cannot be cyclized. The 5-amino-3,4-dicyano-pyrrol-2-thiolate ( 16 ) shows the analogous behaviour. The S-alkylation is followed by cyclization, and 3,5-diamino-thieno[2,3–b]pyrroles ( 18a–b ) arise. Reaction of 5-amino-2-alkylthio-pyrrol-3,5-dicarbonitrile ( 17 ) with acetyl acetone provides pyrrolo[1,2-a]pyrimidine ( 20a–c ) which can be cyclized to form thieno[3′,2′:4,6]pyrimidines ( 21a–c ) very easily. 相似文献
7.
A. M. El-Reedy M. K. A. Ibrahim S. M. Hussain H. H. Moharram 《Advanced Synthesis \u0026amp; Catalysis》1989,331(5):745-750
Acetonedicarboxylic acid dianiline reacted with malononitrile, ethyl cyanoacetate or benzoylacetonitrile to give (6-amino-5-cyano-1,2-dihydro-2-oxo-1-phenylpyrid-4-yl)-acetanilide ( 3 ), (3-cyano-2,6-dioxo-1-phenyl-1,2,5,6-tetrahydropyrid-4-yl)acetanilide ( 8 ) or (3-cyano-1,6-dihydro-1,2-diphenyl-6-oxopyrid-4-yl)acetanilide ( 9 ). Compounds 3 and 8 could be cyclised into 8-amino-1,6-diphenyl-1,2,4,5,6,7-hexahydro-7-iminopyrido[3,4-c]pyridine-2,5-dione ( 4 ) and 7-amino-1,2,3,5,6,8-hexahydro-1,6-diphenylpyrido[3,4-c]pyridine-2,5,8-trione ( 10 ) respectively by heating their solutions in dimethylformamide in the presence of triethylamine. Each of 3 and 4 coupled with arenediazonium chlorides to give the corresponding arylhydrazone derivatives ( 5a–d ) and ( 6a–c ), respectively. Condensation of 4 with p-nitrosodimethylaniline yielded 8-amino-4- (p-dimethylaminophenylimino)-1,6-diphenyl-1,2,4,5,6,7-hexahydro-7-iminopyrido[3,4-c]pyridine2,5-dione ( 7 ). 相似文献
8.
3-phenyl-4-(p-(beta-pyrrolidinoethoxy)- HCl, HC1, 2,2-dimethyl-3-phenyl-4(p-(beta-pyrrolidinoethoxy) -phenyl)-5,6-benzochromene-HCl, 1,1-dimethyl-2,3-diphenyl-4-(beta-pyrrolidinoethoxy) -phenalene, and 1,1-dimethyl-2-phenyl-3-(p-(beta-pyrrolidinoethoxy) -phenyl)-4-beta-pyrrolidinoethoxy phenalene were synthesized from 5,6-benzocoumarins. When tested in rats at 10 mc/kg orally for 5 days for antiimplantation activity, they were ineffective. 相似文献
9.
S. Tumkevicius 《Advanced Synthesis \u0026amp; Catalysis》1994,336(2):160-162
The reaction of ethyl N-(6-ethoxycarbonyl-2-methyl-thiothieno[2,3-d]pyrimidin-5-yl)formimidate ( 1 ) with methyl-hydrazine, N,N′-dimethyl- and N,N′-diphenylhydrazines separately in refluxing ethanol resulted in hydrolysis of formimidate group to give ethyl 5-amino-2-methylthiothieno[2,3-d] pyrimidine-6-carboxylate ( 2 ). The reaction on 1 with methyl-hydrazine without solvent afforded ethyl 5-amino-2-(1-methyl-hydrazino)thieno[2,3-d]pyrimidine-6-carboxylate ( 3 ), which underwent hydrazone formation with p-nitrobenzaldehyde to give 4 . Treatment of 1 with N,N-dimethylhydrazine afforded a mixture of 3-dimethylamino-7-methylthiothieno[2,3-d:4,5-d']dipyrimidin-4(3H)-one ( 5 ) and 2 . Displacement of methylthio group in 5 with morpholine, piperidine and 4-methylpiperazine gave the corresponding 7-substituted derivatives 6a-c . The reaction of 1 with para-substituted phenylhydrazines resulted in the formation of 3-(p-substituted phenylamino)7-methylthiothieno[2,3-d:4,5-d']dipyrimidin-4 (3H)ones ( 7a-c ). 相似文献
10.
以2-氨基-4-氯吡啶为起始原料,经过缩合、取代、环合、乌尔曼反应和水合肼还原硝基5步反应得到中间体4-([1,2,4]三唑并[1,5-a]吡啶-7-氧基)-3-甲基苯胺,总收率28.8%。2-氨基-5-硝基苯腈先与N,N-二甲基甲酰胺二甲基缩醛(DMF-DMA)缩合,再与4-([1,2,4]三唑并[1,5-a]吡啶-7-氧基)-3-甲基苯胺环合得到N-[3-甲基-4-([1,2,4]三唑并[1,5-a]吡啶-7-氧基)苯基]-6-硝基-4-喹唑啉胺,再经硝基还原得到N4-[3-甲基-4-([1,2,4]三唑并[1,5-a]吡啶-7-氧基)苯基]-4,6-喹唑啉二胺,三步收率47.4%。同时,采用二硫化碳和2-氨基-2-甲基-1-丙醇为原料,经两步反应制备4,5-二氢-4,4-二甲基-2-(甲硫基)噁唑三氟甲磺酸盐,收率68.6%。最后,N4-[3-甲基-4-([1,2,4]三唑并[1,5-a]吡啶-7-氧基)苯基]-4,6-喹唑啉二胺和4,5-二氢-4,4-二甲基-2-(甲硫基)噁唑三氟甲磺酸盐以三乙胺为碱进行缩合反应得到妥卡替尼,收率62.8%,HPLC纯度99.08%。采用1HNMR、13CNMR和HRMS等对产物结构进行了表征。该合成路线原料廉价易得,为妥卡替尼的放大生产提供理论依据。 相似文献
11.
Dinesh W. Rangnekar 《Journal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986)》1990,49(4):311-320
4-Nitroso-1-phenyl-3-methyl-5-aminopyrazole ( 1 ) was condensed with ethylcyanoacetate ( 2 ), malononitrile ( 4a ) and 2-cyanomethylbenzimidazole ( 4b ) to yield 6-hydroxy-5-cyano, 6-amino-5-cyano and 6-amino-5-(benzimidazol-2-yl)-3-methylpyrazolo [3,4-b]pyrazines 3, 5a and 5b , respectively. 5-Cyano-6-chloro derivative 6 obtained from 3 was converted to 3-aminopyrazolo[4′,3′:5,6]pyrazino[2,3-c]pyrazoles 8a and 8b by the treatment with hydrazin hydrate ( 7a ) and phenylhydrazine ( 7b ), respectively. Compound 5a was treated with formamide ( 9a ), urea ( 9b ) and thiourea ( 9c ) to give 4-aminopyrazolo[4′,3′:5,6]pyrazino[2′3′-d]pyrimidines 10a–10c. With refluxing acetic anhydride compounds 8a, 8b and 10a gave corresponding acetamido derivatives 8c, 8d and 10d. Compound 5a was treated with ethylorthoformate ( 11 ), acetic anhydride ( 12 ) or benzoylchloride ( 13 ) to give fused benzimidazopyrazolo[4′,3′:5,6]pyrazino[2′,3′-d]pyrimidines, viz., benzimidazol[1,2-c]pyrazolo[4,3-g]pteridines ( 14a–14c ). Some of the compounds 8, 10 and 14 were applied to polyester as disperse dyes and their fastness properties were studied. 相似文献
12.
Vishnu J. Ram 《Advanced Synthesis \u0026amp; Catalysis》1989,331(6):957-963
Various mono and bicyclic pyrimidine analogs ( 3–15 ) were prepared as leishmanicides from 6-aryl-4-chloro-2-methylthiopyrimidine-5-carbonitrile ( 2 ), obtained from the halogenation of 6-aryl-3,4-dihydro-2-methylthio-4-oxopyrimidine-6-carbonitrile ( 1 ). 相似文献
13.
Synthesis of 6-(4-pyridinyI)-substituted Pyrido[2,3-d]pyrimidines and 1,8-Naphthyridinms A series of new 6-(4-pyridinyl)-substituted pyrido-[2,3-d]pyrimidines 2 – 4 and 1,8-naphthyridines 6 , respectively, is described. Cyclisation of 2-amino-5-(4-pyridinyl)-pyridinm-3-carboxamide 1a with diethyl oxalate gives the pyrido-[2,3-d]pyrimidinm 2a . Alkylation of( 2a ) yields the 3-ethylaminoxyrido[2,3-d]pyrimidine derivative 2b . Saponification of 2a , b gives the corresponding carboxylic acids 3a , b , which are decarboxylated by heating above the melting point to give 4a , b . The 2-amino-5-(4-pyridinyl)-pyridinm carboxylic acid derivatives 1 b – e react with ethylmalonylchloridm and diethyl malonate to afford the 1,8-naphthyridines 6b – e . The 1-oxide 7 in a similar reaction gives 8 and the oxdiazole( 9 ) which is converted by ring transformation to the 1,8-naphthyridine 10 . 相似文献
14.
15.
《Journal of Sulfur Chemistry》2013,34(4):329-339
New functionalized pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one derivatives were synthesized via reaction of the hydrazonoyl halides with 7-(4-nitrophenyl)-5-phenyl-2,3-dihydro-2-thioxopyrido[2,3-d]pyrimidin-4(1H)-one or its 2-methylthio derivative. The biological activity of the products has been evaluated. The mechanism and the regioselectivity of the studied reactions have been discussed. 相似文献
16.
《Journal of Sulfur Chemistry》2013,34(3):264-275
A series of novel 3-[6-(4-substituted phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-ylmethyl]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one derivatives (7a–7h) have been synthesized from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (1) through a multi-step reaction sequence. The key intermediate (6) on condensation with various substituted aromatic carboxylic acids in the presence of phosphorus oxychloride afforded the series of title compounds (7a–7h). The structures of all newly synthesized compounds were established on the basis of their IR, 1H-NMR, 13C-NMR and liquid chromatography mass spectrometry spectral data. 相似文献
17.
Mohamed I. Ali M. Amine Abou-State A. Fouad Ibrahim 《Advanced Synthesis \u0026amp; Catalysis》1974,316(1):147-153
2-Methyl-5,6-diphenyl-2,3-dihydro-imidazo[2,1-b]thiazol-3-one 5 and 6,7-diphenyl-2,3-dihydro-4H-imidazo[2,1-b]1,3-thiazin-4-one 6 are prepared from 4,5-diphenyl-2-mercapto-imidazole 1 . Compounds 5 and 6 react with amines or hydrazines to give the 2-(4,5-diphenyl-imidazol-2-ylthio)acet(or propan) amides (hydrazides) 7a – g and the 3-(4,5-diphenyl-imidazol-2 ylthio) propanamides(hydrazides) 8a – e , respectively. The hydrazides 7a, 7b and 8a are condensed with aromatic aldehydes to the hydrazones 9a – h and 10a – d . Compound 5 couples with aryldiazonium salts to give 2-arylazo-2-methyl-5,6-diphenyl-2,3-dihydro-imidazo[2,1-b]thiazol-3-ones 11a – d . 相似文献
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19.
Krystyna Bogdanowicz-Szwed Agnieszka Czarny 《Advanced Synthesis \u0026amp; Catalysis》1993,335(3):279-282
Addition of 1H-benzimidazole-2-carbonitrile ( 1 ) to arylidenemalononitrile ( 2 ) gave 1-amino-3-aryl pyrido[1,2-a]benzimidazole-2,4-dicarbonitrile ( 3 ), 2-aryl-benzimidazole ( 4 ) and 1H-benzimidazole-2-acetonitrile,α-(arylmethylene) ( 5 ). Compounds ( 3 ) reacted with formamide yielding 4-amino-5-aryl pyrimido[5′,4′: 5,6]pyrido[1,2-a]benzimidazole ( 6 ). 相似文献
20.
以1-溴萘为原料,合成了5-溴-7,7-二甲基-7H-苯并[C]芴,总产率为63.1%。其中,对中间体2-(1-萘基)苯甲醛、7-甲基-7H-苯并[C]芴和7,7-二甲基-7H-苯并[C]芴的合成工艺进行了优化。优化反应条件为:2-(1-萘基)苯甲醛合成中,催化剂Pd(dppf)Cl2质量分数3.0%,反应温度40℃,反应时间2 h,产率96.8%;7-甲基-7H-苯并[C]芴合成中,催化剂Amberlyst 15型离子交换树脂的质量分数0.6%,反应温度110℃,反应时间4 h,产率95.4%;7,7-二甲基-7H-苯并[C]芴合成中,n(对甲苯磺酸甲酯)∶n(7-甲基-7H-苯并[C]芴)=2.5∶1,反应温度40℃,产率91.0%。产品结构通过1HNMR和ESI-MS进行了表征。 相似文献