邮政中级考试:吡唑蒽酮合成路线图解

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药物详细合成路线

Chemical Name： Anthra[1,9-cd]pyrazol-6(2H)-one Generic Name：吡唑蒽酮;1,9-Pyrazoloanthrone Other Names： SP-600125 CAS： 129-56-6 Formula： C₁₄H₈N₂O Mole Weight： 220.23266 structure：

Company： Celgene (Originator) Usage： Antiarthritic Drugs, Asthma Therapy, Breast Cancer Therapy, Oncolytic Drugs, RESPIRATORY DRUGS, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, AP-1 Inhibitors, Inhibitors of Signal Transduction Pathways, SAPK1 (JNK) Inhibitors Route 1 The title anthrapyrazolone was synthesized by condensation of 2-chloroanthraquinone (I) with anhydrous hydrazine in pyridine at 100 C. Purification of the compound was achieved via conversion to the N-acetyl derivative, which recrystallized from HOAc, followed by hydrolysis of the acetyl group with ammonium hydroxide in MeOH.

Intermediates: Serial No. (2E,5S,6S,7E,9S)-9-(allyloxy)-5-(2-[1,1-biphenyl]-4-ylethoxy)-1-{[tert-butyl(dimethyl)silyl]oxy}-11-methyl-2,7,11-dodecatrien-6-ol (I) Reference 1: OLeary, E.C.; Satoh, Y.; Manning, A.M.; Bhagwat, S.S.; Bennett, B.L.; Murray, B.W. (Signal Pharmaceuticals, Inc.); Pyrazoloanthrone and derivs. thereof as JNK inhibitors and their compsns.. WO 0112609 .

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