Pyrazolidinediones

The reaction is very common in pyrazolone chemistry. Since alkoxypyrazoles and tautomerizable pyrazolones undergo this reaction and 3-pyrazolin-5-ones, like antipyrine, do not, it is assumed that the reaction takes place at C-4 of the OH tautomer. Pyrazolone diazo coupling is an important industrial reaction since the resulting azo derivatives are used as dyestuffs. For instance, tartrazine (Section 4.04.4.1.3) has been prepared this way. 3,5-Pyrazolidinediones react with aryldiazonium salts resulting in the introduction of a 4-arylazo group. As has been described in Section 4.04.2.1.4(v), diazonium salts couple in the 3-position with indazole to give azo compounds. 

The 3,5-pyrazolidinedione derivatives are an important class of antiinflammatory agents. The most widely used are listed in Table 40. 

Chemical Name 4-butyl-1 -(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione Common Name p-hydroxyphenylbutazone Structural Formula oh... 

Chemical Name 4-butyl-1,2-diphenyl-3,5-pyrazolidinedione Common Name 3,5-dioxo-l, 2-diphenyl-4-n-butylpyrazolidine Structural Formula ... 

Chamical Nama 1,2-diphenvl-4-[2-(phenylsulfinyl)ethyl] -3,5-pyrazolidinedione Common Nama —... 

RN 27315-91-9 MF C25H32N4O2 MW 420.56 EINECS 248-398-7 CN 4-butyl-4-[(4-methyI-l-piperazinyl)methyl]-l,2-diphenyl-3,5-pyrazolidinedione... 

C4H jCl202S 1633-84-7) see Sultiame 4-(3-chloro-2-butenyl)-l,2-diphenyl-3,5-pyrazolidinedione (C11JH17CIN2O2 10561-01-0) see Kebuzone l-chloro-3-(ert-butylamino-2-propanol... 

Sidky, M.M., Soliman, F.M., and Shabana, R., Organophosphorus compounds. XIV. Reaction of dialkyl phosphites and thiol acids with 4-benzylidene-l,2-diphenyl-3,5-pyrazolidinedione, Egypt. J. Chem., 15, 79, 1972. 

Phenylbutazone Phenylbutazone, 4-butyl-l,2-diphenyl-3,5-pyrazolidinedione (3.2.6), is synthesized in a single stage by reacting hydrazobenzol with butylmalonic ester [68,69]. 

Therapeutic Function Antirheumatic, Analgesic, Antiinflammatory Chemical Name 3,5-Pyrazolidinedione, 4-butyl-l-phenyl-Common Name Mofebutazone Monophenylbutazone Mophebutazonum Structural Formula ... 

C27H76FN07 157242-01-8) see Cerivastatin sodium 4-methyl-4-(3,4-dimethoxybenzyl)hydantom (CijH NjO, 892-02-4) see Methyldopa methyl 2-(2,4-dimethoxybenzyloxy)acctate (C jH 60 128685-11-0) see Tacrolimus methyl 3-dimcthylaminoacrylate (QHjjNOj 999-59-7) see Ciprofloxacin 4-[2-(2-methyl-l,3-dioxolan-2-yl)ethyl(-l,2-dipheny 1-3,5-pyrazolidinedione... 

Bonardi G, Vidi A (1973) Action of 4-phenyl-l,2-diphenyl-3,5-pyrazolidinedione (DA 2370) on an experimental hyper-uricosuria in the rat. Pharm Res Comm 5 125-129 Dan T, Yoneya T, Onoma M et al. (1994) Hypouricemic and uricosuric actions of AA-193 in a hyperuricemic rat model. Metabolism 43 123-128... 

C15H12N202 1,4-diphenyl-3,5-pyrazolidinedione 3426-01-5 25.00 1.2538 2 28313 C15HU03 methyl alpha-hydroxydiphenylacetate 76-89-1 25.00 1.1685 2... 

Table 40 Some 3,5-Pyrazolidinedione Derivatives with Biological Activity...

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