- Cyclohexyl-Fused, Spirobiindane-Derived, Phosphine-Catalyzed Synthesis of Tricyclic ?3-Lactams and Kinetic Resolution of ?3-Substituted Allenoates
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A C2-symmetric chiral phosphine catalyst, NUSIOC-Phos, which can be easily derived from cyclohexyl-fused spirobiindane, was introduced. A highly enantioselective domino process involving pyrrolidine-2,3-diones and γ-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic γ-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic γ-substituted allenoates was developed for the generation of optically enriched chiral allenoates.
- Wu, Mingyue,Han, Zhaobin,Li, Kaizhi,Wu, Ji'En,Ding, Kuiling,Lu, Yixin
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- Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity
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The design of rigid cyclic analogues derived from cinnamamide 1, (E)-N-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide, and β-methylcinnamamide 2, (E)-N-cyclopropyl-3-(3-fluorophenyl)but-2-enamide, has led to the discovery of the potent, centrally acting muscle relaxant (E)-2-(4,6-difluoro-1-indanylidene)acetamide, 17. Compound 17 also possesses potent antiinflammatory and analgesic activity. This paper describes the synthesis and the muscle relaxant, antiinflammatory, and analgesic structure-activity relationships of 17 and 67 of its analogues. Compound 17 has been taken into phase I clinical trials.
- Musso, David L.,Cochran, Felicia R.,Kelley, James L.,McLean, Ed W.,Selph, Jeffrey L.,Rigdon, Greg C.,Orr, G. Faye,Davis, Ronda G.,Cooper, Barrett R.,Styles, Virgil L.,Thompson, James B.,Hall, William R.
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p. 399 - 408
(2007/10/03)
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- An N.M.R. Investigation of the Mills-Nixon Effect
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The 4J coupling constant, previously established as a probe of bond order, was used to examine the bond orders in a series of ortho-bridged compounds: benzocyclopropene, 1,2-dihydrobenzocyclobutene, indan and tetralin.No evidence for sterically induced bond fixation (i.e. the Mills-Nixon effect) was found, but some evidence for electronic distortion in the corresponding benzylic ketones was observed.The experimental results are in accord with SCF/MO calculations.
- Collins, Michael J.,Gready, Jill E.,Sternhell, Sever,Tansey, Charles W.
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p. 1547 - 1557
(2007/10/02)
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- Lipoxygenase inhibitory compounds
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Compounds of the formulae STR1 wherein n=6-11, M is hydrogen or a pharmaceutically acceptable cation, R is hydrogen or C1 -C6 alkyl optionally substituted by a carboxyl group and Xa, Xb and Xc each independently represent hydrogen or a variety of substituent groups are potent inhibitors of 5-lipoxygenase.
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