Cell adhesion inhibitors

Rao, N., Meldal, M., Bock, K., and Hindsgaul, O. Library of glyco-peptides useful for identification of cell adhesion inhibitors, Glycomed Corp., 664, 303 [5,795,958], U.S. Patent 1-28, Califomia/USA. 

The same authors have shown that the direct a-amination reaction could also be used to construct the quaternary stereocenter in the enantioselective total synthesis of the cell-adhesion inhibitor BIRT-377 [7b]. The i-proline-derived tetrazole 3c catalyzed the direct a-amination of 3-(4-bromophenyl)-2-methylpropanal 8 with dibenzyl azodicarboxylate 2b to give the amino aldehyde 9 in 95% yield and with... 

Scheme 2.29 The application of organocatalytic enantioselective a-amination reaction of 3-(4-bromophenyl)-2-methylpropanal 8 for the total synthesis of the optically active cell-adhesion inhibitor BIRT-377 [7b].

Disrupts actin cytoskeleton (cell adhesion inhibitor) [attractant feeding deterrent, antineoplastic, cytotoxic] Disrupts actin cytoskeleton blocks cell division by blocking actin microfilament formation [inhibits Glc transport, toxic]... 

Peribysins C and D were initially reported in 2004 as diastereomers that functioned as potent cell adhesion inhibitors from the fungus Periconia byssoides separated from the sea hare Aplysia kurodai These compounds... 

Antiadhesion compounds are expected to be effective in the treatment of metastasis and arthritis. Macrosphelide C (148) was previously reported to be an HL-60 and HUVEC cell adhesion inhibitor, with ICso values of... 

Synthesis of macrosphelides, natural potent cell-cell adhesion inhibitors having novel three ester linkages in their 16-membered macrocyclic skeleton 05H(65)1741, 05Y140. 

Chowdari and Barbas [22] reported the enantioselective total synthesis of potent cell adhesion inhibitor BIRT-377 (56) in 2005, which has potential for the treatment of a number of inflammatory and immune disorders. Asymmetric synthesis of quaternary amino acids is a challenging task for synthetic chemists [23]. Barbas described the efficient L-proUne-derived, tetrazole-catalyzed direct asymmetric a-amination to construct an aldehyde 55 with the amino-substituted quaternary stereocenter and elaborate this aldehyde into BIRT-377 (56) (Scheme 17.7). 

Synthesis of Cell Adhesion Inhibitors via Crystallization-Driven Dynamic Transformations... 

Yamada, T, Iritani, M., Minoura, K., Kawai, K., and Numata, A. (2004) Peribysins A-D, potent cell-adhesion inhibitors from a sea hare derived culture of Periconia species. Org. Biomol. Chem., 2, 2131-2135. 

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