Details

Autor(en) / Beteiligte

• Wang, G X
• Wang, L
• Zhao, Z Z
• Tao, P Z
• Wang, S Q

Titel

Synthesis of optically active (R)- and (S)-tai-ding-an(TDA) and their anti-HSV activity evaluation

Ist Teil von

• Yao hsüeh hsüeh pao, 1996, Vol.31 (11), p.831

Ort / Verlag

China

Erscheinungsjahr

1996

Quelle

MEDLINE

Beschreibungen/Notizen

• Tai-Ding-An (3-phthalimido-2-oxo-n-butyraldehyde bisthiosemicarbazone, TDA) is an antiviral drug first synthesized in this institute. In order to clarify the difference between the two enantiomeric isomers of TDA, (R)- and (S)-TDA were synthesized from (R)- and (S)-alanine, respectively, via the following steps: fusing with phthalic anhydride gave 2-phthalimido alanine(2a or 2b). The resulting acid was reacted with thionyl chloride to offer the corresponding acid chloride(3a or 3b), which was treated with diazomethane to give the diazoketone(4a or 4b). Bromination of the ketone with hydrobromic acid gave the key intermediate 3-phthalimido-2-oxo-1-bromobutanone (5a or 5b). Compound 5a or 5b was oxidized with DMSO to give 6a or 6b, which was directly condensed with thiosemicarbazide to afford the desired (R)- or (S)-TDA. (R)-TDA, (S)-TDA and (RS)-TDA have been tested in cell culture for anti-Herpes simplex virus I (HSV-1) and HSV-2 activities by plaque reducing method. All of them showed inhibitory effects on H