title: Synthesis and Biological Evaluation of 3,5-Dimethoxystilbene Analogs.
abstract: In our continuing effort to discover natural product-based pest management agents, derivatives of 3,5-dimethoxystilbene were synthesized yielding 27 new and six known compounds. Compounds 11 and 12 showed strong Aedes aegypti larvicidal activity (LC5045.31 and 49.93 μm, respectively). Furthermore, 11 and 12 exhibited high effectiveness against larvae of pesticide-susceptible and pyrethroid-resistant strains of Ae. aegypti; activity against the adult mosquitoes was low. Compounds 6f, 6g, and 6i at either 83.3 or 166.7 μg/ml reduced the mobility of second-stage juveniles (J2) of the root-knot nematode (Meloidogyne incognita) that hatched from eggs immersed in the test compounds for 7 days. However, there was little or no effect on J2 placed directly into these compounds, and none of the analogs suppressed M. incognita egg hatch. The compounds were tested for inhibition of some agriculturally important fungi; 6a, 7a, and 7e demonstrated strong inhibition of Colletotrichum species. Activity of the stilbenes against some human pathogens was also explored; 11, 12, and 16 showed moderate inhibitory activity against Cryptococcus neoformans, Staphylococcus aureus, methicillin-resistant S. aureus, and Mycobacterium intracellulare. Except for 11 and 12, which were active against mosquito larvae and some human pathogens, no single analog demonstrated activity in all the tests, indicating specific activities. Synthesis of the analogs and structure-activity relationships are discussed.
authors.affiliation: Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, P.O. Box 1848, University, Mississippi, 38677, USA.
authors.forename: Jian-Quan
authors.initials: JQ
authors.lastname: Weng
authors.affiliation: National Center for Natural Products Research, The University of Mississippi, University, Mississippi, 38677, USA.
authors.forename: Abbas
authors.initials: A
authors.lastname: Ali
authors.affiliation: Mosquito and Fly Research Unit, Center for Medical, Agricultural and Veterinary Entomology, 1600 S.W. 23rd Drive, Gainesville, Florida, 32608, USA.
authors.forename: Alden
authors.initials: A
authors.lastname: Estep
authors.affiliation: Mosquito and Fly Research Unit, Center for Medical, Agricultural and Veterinary Entomology, 1600 S.W. 23rd Drive, Gainesville, Florida, 32608, USA.
authors.forename: James
authors.initials: J
authors.lastname: Becnel
authors.affiliation: Nematology Laboratory, Agricultural Research Service, Henry A. Wallace Beltsville Agricultural Research Center - West, U.S. Department of Agriculture, Beltsville, Maryland, 20705, USA.
authors.forename: Susan L F
authors.initials: SL
authors.lastname: Meyer
authors.affiliation: Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, P.O. Box 1848, University, Mississippi, 38677, USA.
authors.forename: David E
authors.initials: DE
authors.lastname: Wedge
authors.affiliation: National Center for Natural Products Research, The University of Mississippi, University, Mississippi, 38677, USA.
authors.forename: Melissa
authors.initials: M
authors.lastname: Jacob
authors.affiliation: Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, P.O. Box 1848, University, Mississippi, 38677, USA. agnes.rimando@ars.usda.gov.
authors.forename: Agnes M
authors.initials: AM
authors.lastname: Rimando
mesh_terms: D000330:Aedes / Q000187:drug effects*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C000613490:3,5-dimethoxystilbene; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D007306:Insecticides; D013267:Stilbenes
keywords: 
  Aedes aegypti
  ; 
  Colletotrichum
  ; 
  Meloidogyne incognita
  ; 3,5-Dimethoxystilbene analogs; Larvicidal activities