Synthesis and Structure Revision of Dimeric Tadalafil Analogue Adulterants in Dietary Supplements.

作者: Suresh Mandava , Bogonda Ganganna , Jungjoong Hwang , Younchang Jang , Jiho Hwang

DOI: 10.1248/CPB.C17-00034

关键词:

摘要: A number of phosphodiesterase 5 (PDE5) inhibitors approved by authorities have been used successfully in the treatment erectile dysfunction. These medicines must be prescribed carefully due to their adverse effects, but they and analogues are being illegally added dietary supplements. illegal supplements pose a significant risk public health. Several dimeric tadalafil synthesized for use as reference standards inspection functional foods that mainly advertised sexual enhancement products. During course this synthesis, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU) was proven reagent choice amide coupling produce these analogues. Moreover, trans-isomer structures tentatively assigned isolated (bisprehomotadalafil bisprecyclopentyltadalafil) found now revised cis-isomer structures.

参考文章(24)
Ji Hyun Lee, Hyung Joo Kim, Suresh Mandava, Jungjoong Hwang, Hyoung Joon Park, Sooyeul Cho, Sun Young Baek, Jongkook Lee, Identification of a new tadalafil analogue in an adulterated dietary supplement: trans-Bisprehomotadalafil. Journal of Pharmaceutical and Biomedical Analysis. ,vol. 115, pp. 352- 358 ,(2015) , 10.1016/J.JPBA.2015.07.023
Yimin Xu, Chee-Leong Kee, Xiaowei Ge, Min-Yong Low, Hwee-Ling Koh, Isolation and characterization of a tadalafil analogue, N-cyclopentyl nortadalafil in health supplement. Journal of Pharmaceutical and Biomedical Analysis. ,vol. 118, pp. 235- 241 ,(2016) , 10.1016/J.JPBA.2015.08.005
Ji Hyun Lee, Suresh Mandava, Sun Young Baek, Yong-Moon Lee, Identification and structural elucidation of three new tadalafil analogues found in a dietary supplement. Journal of Pharmaceutical and Biomedical Analysis. ,vol. 123, pp. 1- 9 ,(2016) , 10.1016/J.JPBA.2015.10.039
B.J. Venhuis, G. Zomer, M.J. Vredenbregt, D. de Kaste, The identification of (-)-trans-tadalafil, tadalafil, and sildenafil in counterfeit Cialis and the optical purity of tadalafil stereoisomers. Journal of Pharmaceutical and Biomedical Analysis. ,vol. 51, pp. 723- 727 ,(2010) , 10.1016/J.JPBA.2009.08.010
Eric Frérot, Jacques Coste, Antoine Pantaloni, Marie-Noëlle Dufour, Patrick Jouin, PyBOP® and PyBroP: Two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib. Tetrahedron. ,vol. 47, pp. 259- 270 ,(1991) , 10.1016/S0040-4020(01)80922-4
Takashi HASEGAWA, Masaaki SAIJO, Toshiyasu ISHII, Tomoko NAGATA, Yuji HAISHIMA, Nobuo KAWAHARA, Yukihiro GODA, Structural elucidation of a tadalafil analogue found in a dietary supplement. Journal of The Food Hygienic Society of Japan (shokuhin Eiseigaku Zasshi). ,vol. 49, pp. 311- 315 ,(2008) , 10.3358/SHOKUEISHI.49.311
Eung-Sun Lee, Ji Won Kim, Ji Hyun Lee, Kyoung Moon Han, Sooyeul Cho, Insun Hwang, Soon Young Han, Kabyong Chae, Jinho Kim, Identification of a new tadalafil analogue found in a dietary supplement. Food Additives and Contaminants Part A-chemistry Analysis Control Exposure & Risk Assessment. ,vol. 30, pp. 621- 626 ,(2013) , 10.1080/19440049.2013.766766
Alain Daugan, Pascal Grondin, Cécile Ruault, Anne-Charlotte Le Monnier de Gouville, Hervé Coste, Jean Michel Linget, Jorge Kirilovsky, François Hyafil, Richard Labaudinière, The discovery of tadalafil: a novel and highly selective PDE5 inhibitor. 2: 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione analogues. Journal of Medicinal Chemistry. ,vol. 46, pp. 4533- 4542 ,(2003) , 10.1021/JM0300577
Gaofei Zhang, Yue Yu, Xiaoou Wu, Jun Li, Separation and structural elucidation of a new tadalafil analogue diethylaminopretadalafil included as an adulterant in a dietary supplement. Journal of Pharmaceutical and Biomedical Analysis. ,vol. 94, pp. 210- 214 ,(2014) , 10.1016/J.JPBA.2014.01.043
Adrian Häberli, Philippe Girard, Min-Yong Low, Xiaowei Ge, Isolation and structure elucidation of an interaction product of aminotadalafil found in an illegal health food product. Journal of Pharmaceutical and Biomedical Analysis. ,vol. 53, pp. 24- 28 ,(2010) , 10.1016/J.JPBA.2010.03.008