- The total syntheses of JBIR-94 and two synthetic analogs and their cytotoxicities against A549 (CCL-185) human small lung cancer cells
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We here disclose the total syntheses of the natural polyphenol JBIR-94 and two nonnatural analogs, whose structures are of interest for their bioactivity potential as radical scavengers. Although we initially attempted this by dually acylating both of putrecine's amine nitrogens in a single pot, our endeavors with this method (which has been successfully reported by other groups) proved ineffectual. We accordingly opted for the lengthier approach of acylating each amine individually, which gratuitously prevailed and also aligns with separate literature precedent. Moreover, we here share our analysis of these target compounds’ cytotoxicities and IC50 values against A549 (CCL-185) human small lung cancer cells.
- Mangum, Cathy L.,Munford, Mica B.,Sam, Alyssa B.,Young, Sandra K.,Beales, Jeremy T.,Subedi, Yagya Prasad,Mangum, Chad D.,Allen, Tanner J.,Liddell, Miranda S.,Merrell, Andrew I.,Saavedra, Diana I.,Williams, Becky L.,Evans, Nicole,Beales, Joseph L.,Christiansen, Michael A.
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- Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
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A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.
- Pandey, Ganesh,Laha, Ramkrishna,Mondal, Pradip Kumar
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supporting information
p. 9689 - 9692
(2019/08/15)
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- NOVEL ETHER LINKED COMPOUNDS AND IMPROVED TREATMENTS FOR CARDIAC AND CARDIOVASCULAR DISEASE
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A compound of Formula (I), and its pharmaceutically acceptable salt or salts and physiologically hydrolysable derivatives in free form or salt form: wherein R1 is independently selected from F, CI, Br, CN, NH2, OH, CHO, COOH, oxo, C1-4alkyl, C1-4alkoxy, CONH2 (optionally mono- or di-substituted by C1-4alkyl) and SO2NH2, R2 is independently selected from C1-6allkyl substituted by R3 wherein the C1-6alkyl chain optionally comprises one or two heteroatoms select from O; R3 is selected from aryl, C3-6cycloalkyl, C3-6heterocyclyl and C3-6heteroaryl, wherein the heterocyclyl and heteroaryl rings are nitrogen containing; and wherein R3 is optonally substituted by one or more groups selected from R1; n1 is zero or an integer from 1 to 2; n2 is an integer from 1 to 2; and the sum of n1 and 2 is less than or equal to 2; R5 is selected from any group defined for R1 and R2; R6a and R6b are independently selected from H or C1-4alkyl; R7 is independently selected from F, CI, Br, CN, NH2, OH, CHO, COOH, oxo, C1-4alkyl, C1-4alkoxy, CONH2 (optionally mono- or di-substituted by C1-4alkyl) and SO2NH2, Q1, Q2 and Q3 are independently selected from H or any group defined for R1 and R2; or Q1 and Q2 or Q2 and Q3 together form a C5-6heteroaryl or C5-6heterocylclic ring; optionally containing one or two heteroatoms selected from N and O optionally substituted by any group selected from R5; Z is selected from linear C2-3 alkylene; X3 is O; X4 is selected from aryl, a 9-10 membered heteroaryl ring or a 9-10 membered heterocyclic ring, wherein the heteroaryl and heterocyclic rings contain one or more heteroatoms selected from N, and optionally additionally O, and wherein X4 is optionally substituted by one or two oxo moieties and is optionally substituted by one or more groups selected from R7; with the proviso that: (i) when X4 is phenyl then Q1 and Q2 or Q2 and Q3-together form an optionally substituted heteroaryl or heterocylclic ring as defined above; and (ii) when Q1, Q2 and Q3 are independently selected from H or any group defined for R1 and R2 then X4 is not phenyl except when R2 is C1-5alkyl substituted by R3 wherein R3 is C3-6heterocyclyl as defined above.
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Page/Page column 30
(2012/08/27)
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- The biomimetic synthesis and final structure determination of (+)- and (-)-centrolobine, naturally occurring diarylheptanoid 2,6-cis-disubstituted tetrahydro-2H-pyrans
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The enantiomerically pure title compounds were prepared by oxidative cyclization of their optically active diarylheptanoid precursors. The approach is considered as a biomimetic phenol oxidation via an intermediate quinone methide. The absolute configuration of the precursors is retained, and the transition state adopts the sterically most favorable diequatorial arrangement of the 2,6-substituents to afford the cis-configured natural products. The outcome unambiguously establishes the absolute configurations and the correlation with the chiroptical data. In addition, a problem of regioisomerism that had not been discussed before was solved, and the original assignment of the position of the MeO group in the natural centrolobines could be confirmed. As such the results are the experimental evidence for the corrections of long-term inconsistencies we had postulated in an earlier review article.
- Rogano, Frank,Rueedi, Peter
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experimental part
p. 1281 - 1298
(2010/09/12)
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- Synthesis of the alkaloid tyroscherin by an aldol/Curtius strategy
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The alkaloid tyroscherin (2), which contains a vicinal anti-amino alcohol subunit was prepared from 4-hydroxyphenylpropionic acid (5) and meso-diol 9. After desymmetrization of diol 9 and suitable protecting group manipulations, one terminus was extended via a Claisen rearrangement giving rise to enoate ent-15. The missing carbon on the other end could be incorporated using MeMgCl/CuBr·SMe2 leading eventually to aldehyde ent-22. The acylated oxazolidinone 32 derived from acid 5 and aldehyde ent-22 were combined in an aldol reaction. A subsequent Curtius rearrangement on the carboxylic group furnished the amino function of tyroscherin (2). In a proof of concept study the same strategy was used to prepare tyroscherin analog 28.
- Ugele, Markus,Maier, Martin E.
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supporting information; experimental part
p. 2633 - 2641
(2010/05/01)
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- Nonpeptidic HIV protease inhibitors possessing excellent antiviral activities and therapeutic indices. PD 178390: A lead HIV protease inhibitor
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With the insight generated by the availability of X-ray crystal structures of various 5,6-dihydropyran-2-ones bound to HIV PR, inhibitors possessing various alkyl groups at the 6-position of 5,6-dihydropyran-2-one ring were synthesized. The inhibitors pos
- Vara Prasad,Boyer, Frederick E.,Domagala, John M.,Ellsworth, Edmund L.,Gajda, Christopher,Hamilton, Harriet W.,Hagen, Susan E.,Markoski, Larry J.,Steinbaugh, Bruce A.,Tait, Bradley D.,Humblet, Christine,Lunney, Elizabeth A.,Pavlovsky, Alexander,Rubin, John R.,Ferguson, Donna,Graham, Neil,Holler, Tod,Hupe, Donald,Nouhan, Carolyn,Tummino, Peter J.,Urumov,Zeikus, Eric,Zeikus, Greg,Gracheck, Stephen J.,Saunders, James M.,Vanderroest, Steven,Brodfuehrer, Joanne,Iyer,Sinz,Gulnik, Sergei V.,Erickson, John W.
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p. 2775 - 2800
(2007/10/03)
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- Cyclic imino derivatives and pharmaceutical compositions containing them
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The invention relates to cyclic imino compounds which have, inter alia, valuable pharmacological properties, especially inhibitory effects on cell aggregation, pharmaceutical compositions which contain these compounds and processes for preparing them.
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- An easy access to homopropargylic ethers
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Chloromethyl ethers, obtained from alcohols, formaldehyde and HCl, react regioselectively, as shown previously in one case by L.Miginiac, with allenyl aluminium reagents derived from propargyl bromides and aluminium, to give homopropargyl ethers.No evidence for the presence of allenyl ethers was obtained in the cases described.This condensation is used to obtain a protected acetylenic synthon 1, required for the synthesis of an ecdysteroid analogue (1).
- Guedin-Vuong, Denis,Nakatani, Yoichi
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p. 245 - 252
(2007/10/02)
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- SYNTHESIS OF C27-SUBSTITUTED ECDYSTEROIDS, POTENTIAL TOOLS FOR BIOCHEMICAL STUDIES
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A sequence of selective protection procedures is described, facilitating the efficient cleavage of the ecdysteroid side-chain, which can then be reconstructed; in this way, C-27 ether-linked analogues of ecdysteroids have been synthesized, one of which di
- Guedin-Vuong, D.,Nakatani, Y.,Luu, B.,Ourisson, G.
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p. 5959 - 5962
(2007/10/02)
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