Abstract
Petroleum ether-benzene extract of the leaves of Ficus krishnae afforded a novel halogenated 2H-chromen-2-one named 3-chloro-7-methoxy-4-methyl-chromen-2-one. Its structure was established on basis of chemical and physical evidence (IR, 1H NMR, and MS data) as well as on X-ray crystallographic studies.
[1] Abaul, J., Philogène, É., Bourgeois, P., Poupat, C., Ahond, A., & Potier, P. (1994). Contribution à la connaissance des rutacées américaines: Étude des feuilles de Triphasia trifolia. Journal of Natural Products, 57, 846–848. DOI: 10.1021/np50108a028. http://dx.doi.org/10.1021/np50108a02810.1021/np50108a028Search in Google Scholar
[2] Avramenko, L. G., & Nikonov, G. K. (1971). Saxalin-A new furocoumarin from the roots of Angelica saxatilis. Chemistry of Natural Compounds, 7, 804–805. DOI: 10.1007/BF00567948. http://dx.doi.org/10.1007/BF0056794810.1007/BF00567948Search in Google Scholar
[3] Batanero, B., Pérez, M. J., & Barba, F. (1999). Electrosynthesis of 3-chloro-4-substituted-coumarins. Journal of Electroanalytical Chemistry, 469, 201–205. DOI: 10.1016/S0022-0728(99)00198-9. http://dx.doi.org/10.1016/S0022-0728(99)00198-910.1016/S0022-0728(99)00198-9Search in Google Scholar
[4] Beier, R. C., Ivie, G. W., & Oertli, E. H. (1994). Linear furanocoumarins and graveolone from the common herb parsley. Phytochemistry, 36, 869–872. DOI: 10.1016/S0031-9422(00)90453-9. http://dx.doi.org/10.1016/S0031-9422(00)90453-910.1016/S0031-9422(00)90453-9Search in Google Scholar
[5] Billeret, D., Blondeau, D., & Sliwa, H. (1993). Convenient synthesis of 5-azacoumarins. Journal of Heterocyclic Chemistry, 30, 671–674. DOI: 10.1002/jhet.5570300316. http://dx.doi.org/10.1002/jhet.557030031610.1002/jhet.5570300316Search in Google Scholar
[6] Bruker (2003). APEX2 and SAINT. Madison, WI, USA: Bruker AXS Inc. Search in Google Scholar
[7] Chen, Y. L., Wang, T. C., Chang, N. C., Chang, Y. L., Teng, C. M., & Tzeng, C. C. (1998). Alpha-mehtylene-gammabutyrolactones: synthesis and vasorelaxing activity assay of coumarin, naphthalene and quinoline derivatives. Chemical and Pharmaceutical Bulletin, 46, 962–965. 10.1248/cpb.46.962Search in Google Scholar PubMed
[8] Chexal, K. K., Tamm, C., Hirotsu, K., & Clardy, J. (1979). Gilmaniellin and dechlorogilmaniellin, two novel dimeric oxaphenalenones. Helvetica Chimica Acta, 62, 1785–1803. DOI: 10.1002/hlca.19790620611. http://dx.doi.org/10.1002/hlca.1979062061110.1002/hlca.19790620611Search in Google Scholar
[9] de Melo, J. S. S., Becker, R. S., & Macanita, A. L. (1994). Photophysical behavior of coumarins as a function of substitution and solvent: experimental, evidence for the existence of a lowest lying 1(n,.pi.*) state. The Journal of Physical Chemistry, 98, 6054–6058. DOI: 10.1021/j100075a002. http://dx.doi.org/10.1021/j100075a00210.1021/j100075a002Search in Google Scholar
[10] González, A. G., Barroso, J. T., Diaz Chico, E., Luis, J. G., & Rodríguez, L. F. (1976). Compounds of the umbelliferae. XI. New coumarins from Heracleum pyrenaicum Lan. Anales de Química, 72, 584–585. Search in Google Scholar
[11] González, A. G., Barroso, J. T., Luis, J. R., & Rodríguez, L. F. (1974). Compounds of umbelliferae. III. Structure of a new coumarin of Heracleum granatense. Anales de Química, 70, 856–857. Search in Google Scholar
[12] Grover, J. K. (1952). Synthesis of 3-chloro-4-substituted coumarins with a variety of chlorinating agents. Journal of Scientific and Industrial Research, 11B, 50–55. Search in Google Scholar
[13] Ignaťeva, N. S., Vandyshev, V. V., & Pimenov, M. G. (1972). Coumarin from the roots of Cachrys pubescens. Chemistry of Natural Compounds, 3, 381. DOI: 10.1007/BF00563757. http://dx.doi.org/10.1007/BF0056375710.1007/BF00563757Search in Google Scholar
[14] Ilyas, M., Parveen, M., Shafiullah, & Sohrab, M. (1996). Phenolic constituents of Ficus krishnae. Journal of the Indian Chemical Society, 73, 632. Search in Google Scholar
[15] Ito, C., Furukawa, H., Ishii, H., Ishikawa, T., & Haginiwa, J. (1990). The chemical composition of Murraya paniculata. The structure of five new coumarins and one new alkaloid and the stereochemistry of murrangatin and related coumarins. Journal of the Chemical Society, Perkin Transactions 1, 1990, 2047–2055. DOI: 10.1039/P19900002047. http://dx.doi.org/10.1039/p1990000204710.1039/p19900002047Search in Google Scholar
[16] Ivie, G. W. (1978). Linear furocoumarins (psoralens) from the seed of Texas Ammi majus L. (Bishop’s Weed). Journal of Agricultural and Food Chemistry, 26, 1394–1403. DOI: 10.1021/jf60220a023. http://dx.doi.org/10.1021/jf60220a02310.1021/jf60220a023Search in Google Scholar
[17] Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M., & van de Streek, J. (2006). Mercury: visualization and analysis of crystal structures. Journal of Applied Crystallography, 39, 453–457. DOI: 10.1107/S002188980600731X. http://dx.doi.org/10.1107/S002188980600731X10.1107/S002188980600731XSearch in Google Scholar
[18] Parveen, M., Sohrab, M., & Ilyas, M. (1993). Chemical constituents of Ficus krishnae. Journal of the Indian Chemical Society, 70, 785. Search in Google Scholar
[19] Silva, P. S. P., Parveen, M., Ali, A., & Ramos Silva. M. (2011). 8-Iodo-5,7-dimethoxy-4-methyl-2H-chromen-2-one. Acta Crystallographica Section E, 67, o776. DOI: 10.1107/S1600536811007549. http://dx.doi.org/10.1107/S160053681100754910.1107/S1600536811007549Search in Google Scholar
[20] Silva, P. S. P., Parveen, M., Khanam, Z., Ali, A., & Ramos Silva, M. (2010). 6,8-Diiodo-5,7-dimethoxy-4-methylcoumarin. Acta Crystallographica Section E, 66, o988. DOI: 10.1107/S1600536810011360. http://dx.doi.org/10.1107/S160053681001136010.1107/S1600536810011360Search in Google Scholar
[21] Sharma, P. N., Shoeb, A., Kapil, R. S., & Popli, S. P. (1981). Toddanol and toddanone, two coumarins from Toddalia asiatica. Phytochemistry, 20, 335–336. DOI: 10.1016/0031-9422(81)85120-5. http://dx.doi.org/10.1016/0031-9422(81)85120-510.1016/0031-9422(81)85120-5Search in Google Scholar
[22] Sheldrick, G. M. (2003). SADABS, Version 2.10. Göttingen, Germany: University of Göttingen. Search in Google Scholar
[23] Sheldrick, G. M. (2008). A short history of SHELX. Acta Crystallographica Section A, 64, 112–122. DOI: 10.1107/S0108767307043930. http://dx.doi.org/10.1107/S010876730704393010.1107/S0108767307043930Search in Google Scholar
[24] Sood, S., Gupta, B. D., Banerjee, S. K., & Rao, P. R. (1978). Coumarins from the umbels of Prangos pabularia. Journal of the Indian Chemical Society, 55, 850–851. Search in Google Scholar
[25] Thapliyal, P. C., Singh, P. K., & Khanna, R. N. (1994). Copper (II) halides adsorbed on alumina as halogenating reagent for coumarins. ChemInform, 25, 2821–2826. DOI: 10.1002/chin.199416171. 10.1002/chin.199416171Search in Google Scholar
[26] Trost, B. M., Toste, F. D., & Greenman, K. (2003). Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a Net C-H insertion. Journal of the American Chemical Society, 125, 4518–4526. DOI: 10.1021/ja0286573. http://dx.doi.org/10.1021/ja028657310.1021/ja0286573Search in Google Scholar
[27] Zheleva, A. B., Mahandru, M.M., & Bubeva-Ivanova, L. (1976). Four new coumarins from the roots of Peucedanum arenarium. Phytochemistry, 15, 209–210. DOI: 10.1016/S0031-9422(00)89086-X. http://dx.doi.org/10.1016/S0031-9422(00)89086-X10.1016/S0031-9422(00)89086-XSearch in Google Scholar
© 2011 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- 5th conference on membrane science and technology PERMEA 2010
- A procedure for the determination of dichloromethane and tetrachloroethene in water using pervaporation and gas chromatography
- Modeling of diffusive transport of benzoic acid through a liquid membrane
- Comparison of ceramic capillary membrane and ceramic tubular membrane with inserted static mixer
- New approach to regeneration of an ionic liquid containing solvent by molecular distillation
- Mass-transfer in pertraction of butyric acid by phosphonium ionic liquids and dodecane
- Determination of carbon in solidified sodium coolant using new ICP-OES methods
- Interpretation of interactions of halogenated hydrocarbons with modified silica adsorbent coated with 3-benzylketoimine group silane
- Adaptive nonlinear control of a continuous stirred tank reactor
- Anaerobic baffled reactor treatment of biodiesel-processing wastewater with high strength of methanol and glycerol: reactor performance and biogas production
- Analysis of streptolydigin degradation and conversion in cultural supernatants of Streptomyces lydicus AS 4.2501
- Spectroscopic and magnetic evidence of coordination properties of bioactive diethyl (pyridin-4-ylmethyl)phosphate ligand with chloride transition-metal ions
- Microstructure and properties of polyhydroxybutyrate-calcium phosphate cement composites
- Intercalation of basic amino acids into layered zirconium proline-N-methylphosphonate phosphate
- Effect of sol-gel preparation method on particle morphology in pure and nanocomposite PZT thin films
- Synthesis, spectroscopic and configurational study, and ab initio calculations of new diazaphospholanes
- Synthesis and in vitro antimicrobial activity of new 3-(2-morpholinoquinolin-3-yl) substituted acrylonitrile and propanenitrile derivatives
- Silicon-based thiourea-mediated and microwave-assisted thio-Michael addition under solvent-free reaction conditions
- One-pot synthesis of 2-amino-3-cyano-4-arylsubstituted tetrahydrobenzo[b]pyrans catalysed by silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst
- Comparison and optimisation of biodiesel production from Jatropha curcas oil using supercritical methyl acetate and methanol
- Determination of photoredox properties of individual kinetically labile complexes in equilibrium systems
- A halogenated coumarin from Ficus krishnae
- 4β-Isocyanopodophyllotoxins: valuable precursors for the synthesis of new podophyllotoxin analogues
- Environmentally benign one-pot synthesis and antimicrobial activity of 1-methyl-2,6-diarylpiperidin-4-ones
Articles in the same Issue
- 5th conference on membrane science and technology PERMEA 2010
- A procedure for the determination of dichloromethane and tetrachloroethene in water using pervaporation and gas chromatography
- Modeling of diffusive transport of benzoic acid through a liquid membrane
- Comparison of ceramic capillary membrane and ceramic tubular membrane with inserted static mixer
- New approach to regeneration of an ionic liquid containing solvent by molecular distillation
- Mass-transfer in pertraction of butyric acid by phosphonium ionic liquids and dodecane
- Determination of carbon in solidified sodium coolant using new ICP-OES methods
- Interpretation of interactions of halogenated hydrocarbons with modified silica adsorbent coated with 3-benzylketoimine group silane
- Adaptive nonlinear control of a continuous stirred tank reactor
- Anaerobic baffled reactor treatment of biodiesel-processing wastewater with high strength of methanol and glycerol: reactor performance and biogas production
- Analysis of streptolydigin degradation and conversion in cultural supernatants of Streptomyces lydicus AS 4.2501
- Spectroscopic and magnetic evidence of coordination properties of bioactive diethyl (pyridin-4-ylmethyl)phosphate ligand with chloride transition-metal ions
- Microstructure and properties of polyhydroxybutyrate-calcium phosphate cement composites
- Intercalation of basic amino acids into layered zirconium proline-N-methylphosphonate phosphate
- Effect of sol-gel preparation method on particle morphology in pure and nanocomposite PZT thin films
- Synthesis, spectroscopic and configurational study, and ab initio calculations of new diazaphospholanes
- Synthesis and in vitro antimicrobial activity of new 3-(2-morpholinoquinolin-3-yl) substituted acrylonitrile and propanenitrile derivatives
- Silicon-based thiourea-mediated and microwave-assisted thio-Michael addition under solvent-free reaction conditions
- One-pot synthesis of 2-amino-3-cyano-4-arylsubstituted tetrahydrobenzo[b]pyrans catalysed by silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst
- Comparison and optimisation of biodiesel production from Jatropha curcas oil using supercritical methyl acetate and methanol
- Determination of photoredox properties of individual kinetically labile complexes in equilibrium systems
- A halogenated coumarin from Ficus krishnae
- 4β-Isocyanopodophyllotoxins: valuable precursors for the synthesis of new podophyllotoxin analogues
- Environmentally benign one-pot synthesis and antimicrobial activity of 1-methyl-2,6-diarylpiperidin-4-ones