Oxaprostaglandin

An oxaprostaglandin is a type of prostaglandin with one carbon atom replaced by an oxygen atom. These are found in nature and have also been produced synthetically.

11-oxaprostaglandin f2α
11-oxaprostaglandin f2β

Medical uses

A 13-oxaprostaglandin analogue has been shown to treat glaucoma and ocular hypertension.[1] The 11-oxa prostaglandin analogue AL-12182 1 has potent topical ocular hypotensive activity.[2] 7-Oxa-13-prostynoic acid promotes erythrocyte lysis and dissolution of erythrocyte membranes.[3]

Synthesis

11-Oxaprostaglandin f2α and 11-oxaprostaglandin f2β have been synthesized from D-glucose.[4]

References
  1. Feng, Zixia; Hellberg, Mark R.; Sharif, Najam A.; McLaughlin, Marsha A.; Williams, Gary W.; Scott, Daniel; Wallace, Tony (1 January 2009). "Discovery of 13-oxa prostaglandin analogs as antiglaucoma agents: Synthesis and biological activity". Bioorganic & Medicinal Chemistry. 17 (2): 576–584. doi:10.1016/j.bmc.2008.11.070. PMID 19101156.
  2. Fox, Martin E.; Jackson, Mark; Lennon, Ian C.; McCague, Raymond (1 February 2005). "A Convergent Synthesis of the 11-Oxa Prostaglandin Analogue AL-12182". The Journal of Organic Chemistry. 70 (4): 1227–1236. doi:10.1021/jo048035v. PMID 15704955.
  3. Swislocki, Norbert I.; Tierney, Joan; Ritterstein, Susan (1 September 1974). "Disruption of human erythrocytes with 7-oxa-13-prostynoic acid". Prostaglandins. 7 (5): 401–410. doi:10.1016/0090-6980(74)90105-1. PMID 4214491.
  4. Hanessian, Stephen (1983). Total Synthesis of Natural Products: The 'Chiron' Approach. Pergamon press. p. 63. ISBN 978-0-08-029247-2.
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