Dazoxiben

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Dazoxiben
Names
Preferred IUPAC name
4-[2-(1H-Imidazol-1-yl)ethoxy]benzoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
UNII
  • InChI=1S/C12H12N2O3/c15-12(16)10-1-3-11(4-2-10)17-8-7-14-6-5-13-9-14/h1-6,9H,7-8H2,(H,15,16) checkY
    Key: XQGZSYKGWHUSDH-UHFFFAOYSA-N checkY
  • InChI=1/C12H12N2O3/c15-12(16)10-1-3-11(4-2-10)17-8-7-14-6-5-13-9-14/h1-6,9H,7-8H2,(H,15,16)
    Key: XQGZSYKGWHUSDH-UHFFFAOYAY
  • O=C(O)c2ccc(OCCn1ccnc1)cc2
Properties
C12H12N2O3
Molar mass 232.239 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dazoxiben is an orally active thromboxane synthase inhibitor.[1] It has shown a significant clinical improvement in patients with Raynaud's syndrome.[2]

Synthesis[edit]

Dazoxiben synthesis:[3][4][5][6]

One convenient synthesis starts with the O-chloroethyl ether of p-hydroxybenzamide and proceeds bydisplacement with imidazole to give 2. Hydrolysis of the amide function completes the synthesis of dazoxiben.

References[edit]

  1. ^ Belch, J. J.; Cormie, J.; Newman, P.; McLaren, M.; Barbenel, J.; Capell, H.; Leiberman, P.; Forbes, C. D.; Prentice, C. R. (1983). "Dazoxiben, a thromboxane synthetase inhibitor, in the treatment of Raynaud's syndrome: A double-blind trial". British Journal of Clinical Pharmacology. 15 Suppl 1 (Suppl 1): 113S–116S. doi:10.1111/j.1365-2125.1983.tb02119.x. PMC 1427695. PMID 6337601.
  2. ^ Belch, J. J.; Cormie, J.; Newman, P.; McLaren, M.; Barbenel, J.; Capell, H.; Leiberman, P.; Forbes, C. D.; Prentice, C. R. (1983). "Dazoxiben, a thromboxane synthetase inhibitor, in the treatment of Raynaud's syndrome: A double-blind trial". British Journal of Clinical Pharmacology. 15 Suppl 1 (Suppl 1): 113S–116S. doi:10.1111/j.1365-2125.1983.tb02119.x. PMC 1427695. PMID 6337601.
  3. ^ DE 2950019, Cross, Peter Edward & Dickinson, Roger Peter, "Imidazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel [Imidazol derivatives, processes for their production and pharmaceuticals containing them]", published 1980-07-10, assigned to Pfizer Corp. 
  4. ^ Kochergin, P. M.; Palei, R. M.; Balandina, L. V.; Kharitonova, A. E.; Kravchenko, A. N.; Persanova, L. V.; Govorukhina, E. I.; Frolova, M. A. (1995). "Simplified synthesis of dazoxiben". Pharmaceutical Chemistry Journal. 29 (2): 139. doi:10.1007/BF02226528. S2CID 37387182.
  5. ^ Iizuka, Kinji; Akahane, Kenji; Momose, Denichi; Nakazawa, Masayuki; Tanouchi, Tadao; Kawamura, Masanori; Ohyama, Isao; Kajiwara, Ikuo; Iguchi, Yohichi (1981). "Highly selective inhibitors of thromboxane synthetase. 1. Imidazole derivatives". Journal of Medicinal Chemistry. 24 (10): 1139–1148. doi:10.1021/jm00142a005. PMID 7199088.
  6. ^ Cross, Peter E.; Dickinson, Roger P.; Parry, M. John; Randall, Michael J. (1985). "Selective thromboxane synthetase inhibitors. 1. 1-[(Aryloxy)alkyl]-1H-imidazoles". Journal of Medicinal Chemistry. 28 (10): 1427–1432. doi:10.1021/jm00148a009. PMID 3930740.


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