title: Total synthesis and bioactivity of the marine alkaloid pityriacitrin and some of its derivatives.
abstract: We report herein the chemical synthesis and biological evaluation of β-carboline alkaloid pityriacitrin and some of its new derivatives. Using tryptophan or 5-hydroxytryptophan and 5-substituted indole-3-glyoxals as the starting materials, pityriacitrin and some of its derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by (1)H and (13)C NMR, mass spectroscopy and IR determinations. Biological studies revealed that pityriacitrin has a weak antiproliferative activity against a panel of breast and prostate cancer cell lines, whereas some of its derivatives exhibited stronger and potent activity, which was associated with induction of both cell apoptosis and necrosis.
authors: School of Medicine and Pharmacy, Key Laboratory of Marine Drugs, Ministry of Education, Ocean University of China, Qingdao, China.
authors: Puyong
authors: P
authors: Zhang
authors: Xiaofei
authors: X
authors: Sun
authors: Bin
authors: B
authors: Xu
authors: Krikor
authors: K
authors: Bijian
authors: Shengbiao
authors: S
authors: Wan
authors: Guigen
authors: G
authors: Li
authors: Moulay
authors: M
authors: Alaoui-Jamali
authors: Tao
authors: T
authors: Jiang
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005260:Female; D006801:Humans; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008290:Malassezia / Q000737:chemistry; D008297:Male; D011471:Prostatic Neoplasms / Q000188:drug therapy
chemical_list: D000970:Antineoplastic Agents; D026121:Indole Alkaloids; C470985:pityriacitrin