Efficient synthesis of dichlorodenafil, an unapproved sildenafil analogue appearing in non-prescription supplements

Jong Yup Kim, In Gyun Hwang, Jae Ho Oh, Il Hyun Kang, Sung Won Kwon, Deukjoon Kim

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

We have developed an efficient synthesis of dichlorodenafil (4), an unapproved sildenafil analogue isolated from dietary supplements. Our sequence employs POCl3-mediated chlorination of readily available chloroacetyl compound 7 followed by selective hydrolysis of the chloro-heterocycle function. Our synthesis confirms the structure of the illegal additive, and will provide regulatory agencies with ready access to authentic standard samples of dichlorodenafil (4) to aid in their mission to protect the public from unapproved and potentially harmful erectile dysfunction (ED) drug analogues that are added to herbal and dietary supplements without providing users with appropriate toxicological or pharmacological information.

Original languageEnglish (US)
Pages (from-to)572-575
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume61
Issue number5
DOIs
StatePublished - May 2013

Fingerprint

Dietary supplements
Dietary Supplements
Chlorination
Halogenation
Erectile Dysfunction
Toxicology
Hydrolysis
Pharmacology
Pharmaceutical Preparations
dichlorodenafil
Sildenafil Citrate

Keywords

  • Dichlorodenafil
  • Illegal food additive
  • Sildenafil analogue
  • Synthesis

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

Efficient synthesis of dichlorodenafil, an unapproved sildenafil analogue appearing in non-prescription supplements. / Kim, Jong Yup; Hwang, In Gyun; Oh, Jae Ho; Kang, Il Hyun; Kwon, Sung Won; Kim, Deukjoon.

In: Chemical and Pharmaceutical Bulletin, Vol. 61, No. 5, 05.2013, p. 572-575.

Research output: Contribution to journalArticle

Kim, Jong Yup ; Hwang, In Gyun ; Oh, Jae Ho ; Kang, Il Hyun ; Kwon, Sung Won ; Kim, Deukjoon. / Efficient synthesis of dichlorodenafil, an unapproved sildenafil analogue appearing in non-prescription supplements. In: Chemical and Pharmaceutical Bulletin. 2013 ; Vol. 61, No. 5. pp. 572-575.
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