Pyrabactin

Pyrabactin
Names
Preferred IUPAC name
4-Bromo-N-[(pyridin-2-yl)methyl]naphthalene-1-sulfonamide
Other names
4-Bromo-N-(pyridin-2-ylmethyl)naphthalene-1-sulfonamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.212.933
UNII
  • InChI=1S/C16H13BrN2O2S/c17-15-8-9-16(14-7-2-1-6-13(14)15)22(20,21)19-11-12-5-3-4-10-18-12/h1-10,19H,11H2
    Key: GJSDYQXOSHKOGX-UHFFFAOYSA-N
  • InChI=1/C16H13BrN2O2S/c17-15-8-9-16(14-7-2-1-6-13(14)15)22(20,21)19-11-12-5-3-4-10-18-12/h1-10,19H,11H2
    Key: GJSDYQXOSHKOGX-UHFFFAOYAQ
  • Brc2c1c(cccc1)c(cc2)S(=O)(=O)NCc3ncccc3
Properties
C16H13BrN2O2S
Molar mass 377.26 g·mol−1
Appearance White to off-white powder[1]
Solubility in DMSO >10 mg/mL[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pyrabactin is a synthetic sulfonamide that mimics abscisic acid (ABA), a naturally produced stress hormone in plants that helps them cope with drought conditions by inhibiting growth. ABA can be manufactured for agricultural use; however, ABA is light-sensitive and costly to make. Pyrabactin is relatively inexpensive, easy to make, and not sensitive to light. Unlike ABA, pyrabactin activates only a few of the 14 ABA receptors in the plant needed for effective drought tolerance.[2] Its role as an ABA mimic may make pyrabactin an important tool for protecting crops against drought and cold weather.[3][4]

The discovery of pyrabactin by Sean Cutler was named a breakthrough research of 2009 by Science magazine.[5]

Pyrabactin (for pyridyl containing ABA activator) is a naphthalene sulfonamide hypocotyl cell expansion inhibitor. A combination of genetic, transcriptomic and physiological evidence demonstrated that pyrabactin activates the ABA pathway in a manner very similar to ABA. As such, pyrabactin is the first ABA agonist that is not an ABA analog and may ultimately lead to the development of a new family of synthetic plant growth regulators.




References
  1. Pyrabactin, Sigma-Aldrich
  2. Organic compound comes to the aid of thirsty plants, Royal Society of Chemistry, 1 May 2009
  3. Pyrabactin - American Chemical Society
  4. Synthetic chemical offers solution for crops facing drought
  5. Growing drought-tolerant crops inching forward (Science Blog)
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