178
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis, Absolute Configuration and Biological Activities of Both Enantiomers of 2-(5,7-Dichloro-3-indolyl)propionic Acid: a Novel Dichloroindole Auxin and Antiauxin

, &
Pages 1287-1292 | Received 08 Jan 2004, Accepted 21 Feb 2004, Published online: 22 May 2014

  • 1) Marumo, S., Hattori, H., Abe, H., and Munakata, K., Isolation of 4-chloroindolyl-3-acetic acid from immature seeds of Pisum sativum. Nature, 214, 959–960 (1968).
  • 2) Marumo, S., Abe, H., Hattori, H., and Munakata, K., Isolation of a novel auxin, methyl 4-chloroindoleacetate from immature seeds of Pisum sativum. Agric. Biol. Chem., 32, 117–118 (1968).
  • 3) Katayama, M., Synthesis and biological activities of 4-chloroindole-3-acetic acid and its esters. Biosci. Biotechnol. Biochem., 64, 808–815 (2000).
  • 4) Katayama, M., Hattori, H., and Kamuro, Y., Plant growth-regulating activities of 4-chloroindole-3-acetic acid and its esters. J. Pesticide Sci., 27, 68–70 (2002).
  • 5) Katayama, M., Development of root formation promoters and their utilization. Green Age, 21, 12–13 (2000).
  • 6) Hatano, T., Katayama, M., and Marumo, S., 5,6-Dichloroindole-3-acetic acid as a potent auxin: its synthesis and biological activity. Experientia, 43, 1237–1239 (1987).
  • 7) Katayama, K., and Futatsuya, F., Synthesis and biological activities of chlorinated indole auxins and antiauxins. Plant Cell Technology (in Japanese with English abstract), 2, 487–502 (1990).
  • 8) Katayama, M., Studies on chlorinated indole auxins and antiauxins. Chemical Regulation of Plants (in Japanese), 26, 11–24 (1991).
  • 9) Hatano, T., Kato, Y., Katayama, M., and Marumo, S., A new indole antiauxin, α-(5,7-dichloroindole-3-)isobutyric acid: its chemical synthesis and biological activity. Experientia, 45, 400–402 (1989).
  • 10) Katayama, M., Kato, K., Kimoto, H., and Fujii, S., (S)-(+)-4,4,4-Trifluoro-3-(indole-3-)butyric acid, a novel fluorinated plant growth regulator. Experientia, 51, 721–724 (1995).
  • 11) Katayama, M., and Gautam, R. K., Synthesis and biological activities of substituted 4,4,4-trifluoro-3-(indole-3-)butyric acids, novel fluorinated plant growth regulators. Biosci. Biotechnol. Biochem., 60, 755–759 (1996).
  • 12) Katayama, M., and Gautam, R. K., Synthesis and biological activities of fluorinated plant growth regulators, 4,4,4-trifluoro-3-(3-indolyl)butyric acids and 4,4,4-trifluoro-3-(2-indolyl)butyric acid bearing a methyl group on the indole nucleus. J. Pesticide Sci., 22, 331–337 (1997).
  • 13) Katayama, M., Kato, Y., Hatano, T., Hatori, M., and Marumo, S., Synthesis and biological activities of 5,6-difluoroindole-3-acetic acid; a new fluoroindole auxin. J. Pesticide Sci., 23, 289–295 (1998).
  • 14) Sjöberg, B., Stereochemical studies. III. Resolution and configuration of α-(3-indolyl)-propionic acid. Arkiv för Kemi, 12, 251–258 (1957).
  • 15) Kögl, F., and Verkaaik, B., Über die Antipoden der α-(β′ Indolyl)-propionsäure und ihre verschieden starke physiologische Wirksamkeit. Z. Physiol. Chem., 280, 167–176 (1944).
  • 16) Sjöberg, B., Stereochemical studies. VI. Steric relations of some α-arylpropionic acids. Arkiv för Kemi, 13, 1–10 (1958).
  • 17) Kögl, F., Wirkstoffprinzip und Planzenwachstum. Naturwissenschaften, 25, 465–470 (1937).
  • 18) Katayama, M., Kato, Y., and Marumo, S., Synthesis, absolute configuration and biological activity of both enantiomers of 2-(5,6-dichloro-3-indolyl)propionic acid: new dichloroindole auxins. Biosci. Biotechnol. Biochem., 65, 270–276 (2001).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.