Synthesis and reactions of some pyridazine derivatives

Khalifa, F. A.

doi:10.1007/bf02857800

Cited by 5 publications

(11 citation statements)

References 3 publications

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“…Unless stated otherwise, starting materials used were high-grade commercial products. The following products were prepared according to the literature: 3-amino-4,5-diphenyl-1H-pyrazolo [3,4-c]pyridazine 1a, 20 3-amino-4,5-dimethyl-1Hpyrazolo [3,4-c]pyridazine 1j, 21 4,5-diphenyl-1H-pyrazolo [3,4c]pyridazin-3-ol 2a. 14 Complete 1 H and 13 C NMR, IR, MS, and elemental analysis data are given in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

“…1-(4,5-Diphenyl-1H-pyrazolo[3,4-c]pyridazin-3-yl)-3ethylurea (2b). From ethyl isocyanate (48 mg, 0.68 mmol) in anhydrous CH 2Cl2 (1 mL) and 1a 20 (180 mg, 0.68 mmol) in a mixture of CH2Cl2/THF 5:3 (8 mL) was obtained 2b (174 mg, 72%) as a red solid isolated by concentrating the solvent under vacuum, mp 132-134 °C. IR (KBr): 1715, 3310, 3350, 3460 cm -1 .…”

Section: -Amino-3h-dibenzo[fh]pyrazolo[34-c]cinnoline (1g)mentioning

confidence: 99%

“…From phenyl isocyanate (0.076 mL, 0.70 mmol) in anhydrous CH2Cl2 (1 mL) and 1a 20 (200 mg, 0.70 mmol) in a mixture of CH2Cl2/THF 5:3 (5 mL) was obtained 2c (94 mg, 33%) as a yellow solid isolated by filtration, mp 239-241 °C.…”

Section: -(45-diphenyl-1h-pyrazolo[34-c]pyridazin-3-yl)-3phenylurea (2c)mentioning

confidence: 99%

“…A suspension of 1a 20 (0.50 g, 1.74 mmol) in H2O (2 mL) was added dropwise to a solution of NaNO2 (120 mg, 1.74 mmol) and concentrated HCl in H2O (2 mL) at 0 °C for 48 h. After cooling, the formed solid was filtered under vacuum and purified by recrystallization from absolute EtOH to give 2d (760 mg, 75%), mp 134-136 °C. IR (KBr): 3190, 3290, 3440 cm -1 .…”

Section: 5-diphenyl-1h-pyrazolo[34-c]pyridazin-3-yl)hydrazine Trihydr...mentioning

confidence: 99%

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Pyrazolo[3,4-c]pyridazines as Novel and Selective Inhibitors of Cyclin-Dependent Kinases

et al. 2005

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Pyrazolopyridazine 1a was identified in a high-throughput screening carried out by BASF Bioresearch Corp. (Worcester, MA) as a potent inhibitor of CDK1/cyclin B and shown to have selectivity for the CDK family. Analogues of the lead compound have been synthesized and their antitumor activities have been tested. A molecular model of the complex between the lead compound and the CDK2 ATP binding site has been built using a combination of conformational search and automated docking techniques. The stability of the resulting complex has been assessed by molecular dynamics simulations and the experimental results obtained for the synthesized analogues have been rationalized on the basis of the proposed binding mode for compound 1a. As a result of the SAR study, monofuryl 1o has been synthesized and is one of the most active compounds against CDK1 of this series.

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Section: Methodsmentioning

confidence: 99%

Section: -Amino-3h-dibenzo[fh]pyrazolo[34-c]cinnoline (1g)mentioning

confidence: 99%

Section: -(45-diphenyl-1h-pyrazolo[34-c]pyridazin-3-yl)-3phenylurea (2c)mentioning

confidence: 99%

Section: 5-diphenyl-1h-pyrazolo[34-c]pyridazin-3-yl)hydrazine Trihydr...mentioning

confidence: 99%

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Pyrazolo[3,4-c]pyridazines as Novel and Selective Inhibitors of Cyclin-Dependent Kinases

et al. 2005

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“…A great number of other examples of the use of cyanoacetamides and their S-and Se-derivatives in the synthesis of functionalised 3-cyanopyridin-2(1H)-ones, -thiones and -selenones, 560 ± 604 3-cyanopyridin-2-olates and -thiolates, 605 ± 609 pyrimidin-2-ones, 610 ± 616 tetrahydroquinolin-2-ones, 617, 618 5-cyano-3,4-diphenylpyridazin-6-one, 619 2-aryl-5-cyano-4-methylthio-1,3oxazin-6-ones 620 and other heterocyclic compounds are also documented. Cyanoacetamides 1a,b have found application in the synthesis of substituted pyridines 282, 621 quinolines 178, 438 283, 622 284, 623, 624 isoquinolines 285, 388,389,625 286, 626 pyrazine 287, 627 dihydropyrrolopyrimidines 288 628 and triazines 289.…”

Section: -Substitutedmentioning

confidence: 99%