Synthesis and in vitro study of pseudo-peptide thioureas containing α-aminophosphonate moiety as potential antitumor agents.
Twenty pseudo-peptide thioureas IIa-l containing α-aminophosphonate moiety were synthesized from the reaction of chiral α-amino carboxamide derivatives Ia-c with O,O'-dialkylisothiocyanato(phenyl)methylphosphonate 5. The synthesized compounds were completely characterized by elemental analysis, physical and spectral (IR, (1)H NMR, (13)C NMR) data. According to the preliminary studies on antitumor activities, compounds IIa-l could inhibit tumor cells PC3, Bcap37 and BGC823. These compounds displayed low to high activity by MTT assays. Among them, L-IIk, D-IIa and D-IIe were identified as potent inhibitors, with IC(50) values ranging from 4.7 to 11.2 μM according to in vitro assay.
Liu
Jing-Zi
JZ
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, PR China.
Song
Bao-An
BA
Fan
Hui-Tao
HT
Bhadury
Pinaki S
PS
Wan
Wen-Ting
WT
Yang
Song
S
Xu
Weiming
W
Wu
Jian
J
Jin
Lin-Hong
LH
Wei
Xue
X
Hu
De-Yu
DY
Zeng
Song
S
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000737:chemistry*; D000091402:Prohibitins; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013890:Thiourea / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000970:Antineoplastic Agents; D063065:Organophosphonates; C000717331:PHB2 protein, human; D000091402:Prohibitins; D013890:Thiourea