-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】3-(4-Phenylsulfanylphenylsulfonyl)-1-propanethiol

【CA登记号】202665-40-5

【分子式】C₁₅H₁₆O₂S₃

【分子量】324.48557

【开发单位】Pfizer (Originator)

【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Matrix Metalloproteinase Inhibitors

合成路线1

Alkylation of 4-fluorothiophenol (I) with 3-chloropropanol (II) in the presence of K2CO3 in DMF provided thioether (III), which was oxidized to sulfone (IV) using Oxone(R). Fluorine displacement in (IV) with thiophenol and K2CO3 gave phenylsulfanyl derivative (V). The hydroxyl group of (V) was converted to mesylate (VI) and then displaced by potassium thioacetate to afford thioacetate ester (VII). Finally, hydrolysis with methanolic NaOMe furnished the target thiol.

参考文献中间体

【1】 Inturrisi, C.E.; Collins, J.J.; Dunkel, I.J.; Portenoy, R.K.; Palmer, L.N.; Lapin, J.; Gupta, S.K.; Weinstein, S.M.; Transdermal fentanyl in children with cancer pain: Feasibility, tolerability, and pharmacokinetic correlates. J Pediatr 1999, 134, 3, 319.
【2】 Freskos, J.N.; Abbas, Z.S.; Decrescenzo, G.A.; Getman, D.P.; Heintz, R.M.; Mischke, B.V.; McDonald, J.J. (Pharmacia Corp.); Thiol sulfone metalloprotease inhibitors. EP 0939628; WO 9803164 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	12951	Benzenethiol; Phenylmercaptan; Phenylhydrosulfide	108-98-5	C₆H₆S	详情	详情
(I)	22971	4-fluorobenzenethiol; 4-fluorophenylhydrosulfide; 4-Fluorothiophenol	371-42-6	C₆H₅FS	详情	详情
(II)	19490	3-chloro-1-propanol	627-30-5	C₃H₇ClO	详情	详情
(III)	27076	3-[(4-fluorophenyl)sulfanyl]-1-propanol		C₉H₁₁FOS	详情	详情
(IV)	27077	3-[(4-fluorophenyl)sulfonyl]-1-propanol		C₉H₁₁FO₃S	详情	详情
(V)	27078	3-[(4-phenoxyphenyl)sulfonyl]-1-propanol		C₁₅H₁₆O₄S	详情	详情
(VI)	27083	3-[[4-(phenylsulfanyl)phenyl]sulfonyl]propyl methanesulfonate		C₁₆H₁₈O₅S₃	详情	详情
(VII)	27084	S-(3-[[4-(phenylsulfanyl)phenyl]sulfonyl]propyl) ethanethioate		C₁₇H₁₈O₃S₃	详情	详情

Extended Information