- The synthesis and electronic absorption spectra of 3-phenyl-3(4- pyrrolidino-2-substituted phenyl)-3H-naphtho[2,1-b]pyrans: Further exploration of the ortho substituent effect
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Introduction of a substituent into a sterically demanding 2-position of a 3-(4-pyrrolidinophenyl) ring of a 3,3-diaryl-3H-naphtho[2,1-b]pyran results in the generation of an additional short wavelength absorption band leading to organic photochromes that
- Gabbutt, Christopher D.,Heron, B. Mark,Instone, Alicia C.
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p. 737 - 745
(2007/10/03)
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- Acyl sulfonamide anti-proliferatives: Benzene substituent structure-activity relationships for a novel class of antitumor agents
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Two closely related diaryl acylsulfonamides were recently reported as potent antitumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. Especially intriguing was their activity against colorectal cancer xenografts. In this paper, rapid parallel synthesis along with traditional medicinal chemistry techniques were used to quickly delineate the structure-activity relationships of the substitution patterns in both phenyl rings of the acylsufonamide anti-proliferative scaffold. Although the molecular target of the compounds remains unclear, we determined that the vascular endothelial growth factor-dependent human umbilical vein endothelial cells assay in combination with a soft agar disk diffusion assay allowed for optimization of potency in the series. The pharmacokinetic properties and in vivo activity in an HCT116 xenograft model are reported for representative compounds.
- Lobb, Karen L.,Hipskind, Philip A.,Aikins, James A.,Alvarez, Enrique,Cheung, Yiu-Yin,Considine, Eileen L.,De Dios, Alfonso,Durst, Gregory L.,Ferritto, Rafael,Grossman, Cora Sue,Giera, Deborah D.,Hollister, Beth A.,Huang, Zhongping,Iversen, Philip W.,Law, Kevin L.,Li, Tiechao,Lin, Ho-Shen,Lopez, Beatriz,Lopez, Jose E.,Martin Cabrejas, Luisa M.,McCann, Denis J.,Molero, Victoriano,Reilly, John E.,Richett, Michael E.,Shih, Chuan,Teicher, Beverly,Wikel, James H.,White, Wesley T.,Mader, Mary M.
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p. 5367 - 5380
(2007/10/03)
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- Application of Organolithium and Related Reagents in Synthesis XVI: Synthetic Strategies Based on Aromatic Metallation. A Concise Regiospecific Conversion of Chlorobenzoic Acids into their Benzylated Derivatives
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The reaction of benzyl bromide with bis-(N- and C-ortho)-lithiated chloroanilides 4, 5, and 6 has been examined.It has been found that in the case where the lithiated compound was derived from meta-methoxyanilides, pre-addition of LiBr or TMEDA was required to achieve C-benzylation.These results were accounted for by the conversion of the usually formed dimer into a mixed dimer with the LiBr or TMEDA complex in which the C-lithium bond appears to be more accessible towards electrophiles.The practical synthesis of o-benzylchlorobenzoic acids 10, 11, and 12 was accomplished via ionic reductive cleavage (Et3SiH/TiCl4) of the corresponding phthalides 18, 19, and 20.The acids 10, 11b, and 11c afforded the corresponding anthrones, upon treatment with trifluoroacetic anhydride which were oxidized by chromium trioxide to the new chloroantraquinones 21, 22, and 23. - Keywords: Chlorophthalides; Reduction; Benzylation; Benzylbenzoic acids; Chloroantraquinones
- Epsztajn, J.,Bieniek, A.,Kowalska, J. A.
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p. 701 - 716
(2007/10/03)
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