Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines.
Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.
Peterson
J R
JR
Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University 38677.
Zjawiony
J K
JK
Liu
S
S
Hufford
C D
CD
Clark
A M
AM
Rogers
R D
RD
D017088:AIDS-Related Opportunistic Infections / Q000382:microbiology; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001060:Aporphines; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D015269:Mycobacterium avium Complex / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001060:Aporphines; C064232:3-methoxysampangine