Cinnamamide - CAS 22031-64-7
Catalog number: 22031-64-7
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Cinnamamide also called 3-Phenyl-2-propenamide, is natural phenylpropanoid isolated from the root of Kaempferia galangal L,3-Phenyl-2-propenamide derivatives exhibits therapeutic potential in animal models of both central and peripheral nervous system disorders.
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1.Bicyclic compounds as ring-constrained inhibitors of protein-tyrosine kinase p56lck.
Burke TR Jr;Lim B;Marquez VE;Li ZH;Bolen JB;Stefanova I;Horak ID J Med Chem. 1993 Feb 19;36(4):425-32.
A study was undertaken to prepare inhibitors of the lymphocyte protein-tyrosine kinase p56lck. Using the known p56lck inhibitor 3,4-dihydroxy-alpha-cyanocinnamamide (4) as a lead compound, bicyclic analogues were designed as conformationally constrained mimetics in which the phenyl ring and vinyl side chain of the cinnamamide are locked into a coplanar orientation. Such planarity was rationalized to be an important determinant for binding within a putative flat, cleftlike catalytic cavity. Bicyclic analogues were prepared using the naphthalene, quinoline, isoquinoline, and 2-iminochromene ring systems and examined for their ability to inhibit autophosphorylation of immunopurified p56lck. The most potent analogues were methyl 7,8-dihydroxyisoquinoline-3-carboxylate (12) (IC50 = 0.2 microM) and 7,8-dihydroxyisoquinoline-3-carboxamide (13) (IC50 = 0.5 microM). Inhibition by 12 was not competitive with respect to ATP. These compounds may represent important new structural motifs for the development of p56lck inhibitors.
2.Aminochlorination in water: first Brønsted acid-promoted synthesis of vicinal chloramines.
Wu XL;Wang GW J Org Chem. 2007 Nov 23;72(24):9398-401. Epub 2007 Oct 31.
A practical and scaleable route for the regio- and diastereoselective synthesis of vicinal chloramines from electron-deficient olefins and Chloramine-T promoted by Brønsted acids in water has been realized for the first time. This novel protocol is efficient, mild, ecofriendly, and broadly applicable for the aminochlorination of various electron-deficient olefins including alpha,beta-unsaturated ketones, cinnamate, and cinnamide. Water represents as a privileged solvent for the aminochlorination reaction in our system.
3.The histamine amides of Acacia longifolia.
Repke DB Lloydia. 1975 Mar-Apr;38(2):101-5.
Extracts of Acacia longifolia yielded two major histamine aldaloiks which were separated by tlc. Nmr, ms, uv, ir and other physical measurements led to structural assignments of the compounds as N-(2-imidazol-4-yl-ethyl)-trans-cinnamamide and N-(2-imidazol-4-yl-ethyl)-deca-trans-2, cis-4-dienamide. Confirmation of these structures was by comparison of literature data in the case of the cinnamamide and by synthesis of the new decadienamide. Dowex-50 ion exchange resin (H+ form) was found to be highly efficient in the isolation of these compounds from crude plant extracts.
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