- Anti-AIDS agents 73: Structure-activity relationship study and asymmetric synthesis of 3-O-monomethylsuccinyl-betulinic acid derivatives
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3-O-3′(or 2′)-Methylsuccinyl-betulinic acid (MSB) derivatives were separated by using recycle HPLC. The structures of four isomers were assigned by NMR and asymmetric synthesis. 3-O-3′S-Methylsuccinyl-betulinic acid (3′S-MSB, 4) exhibited potent anti-HIV
- Qian, Keduo,Nakagawa-Goto, Kyoko,Yu, Donglei,Morris-Natschke, Susan L.,Nitz, Theodore J.,Kilgore, Nicole,Allaway, Graham P.,Lee, Kuo-Hsiung
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Read Online
- 3,6-DIAMINO-PYRIDAZIN-3-YL DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USES AS PRO-APOPTOTIC AGENTS
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Compounds of formula (I) wherein Het1, Het2, R1, R2 and R3 are as defined in the description. Medicaments.
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Page/Page column 102-103
(2021/02/05)
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- Remote chiral communication in coadsorber-induced enantioselective 2D supramolecular assembly at a liquid/solid interface
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Remote chiral communication in 2D supramolecular assembly at a liquid/solid interface was investigated at the molecular level. The stereochemical information in a chiral coadsorber was transmitted over a flexible spacer with a length of up to five methylene groups to a 2D supramolecular assembly of achiral building blocks with the cooperation of specific hydrogen bonding between the chiral coadsorber and achiral building blocks and the confinement effect during 2D crystallization. When the position of the stereogenic center was changed with respect to the stereocontrolling moiety, an odd-even effect was found. A stereogenic center closer to the stereocontrolling moiety transmitted the stereochemical information to the 2D supramolecular assembly more reliably. This result is beneficial not only for mechanistic understanding of chiral communication in 2D supramolecular assembly on surfaces but also for the rational design of homochiral supramolecular assemblies on surfaces.
- Chen, Ting,Li, Shu-Ying,Wang, Dong,Yao, Man,Wan, Li-Jun
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supporting information
p. 4309 - 4314
(2015/04/14)
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- 3-(BIARYLOXY) PROPIONIC ACID DERIVATIVE
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A compound of the general formula (I): [wherein, R1 represents a halogen atom, or the like, R2 represents a hydrogen atom, or the like, R3 and R4, each independently, represent a hydrogen atom, a C1-4
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Page/Page column 56
(2012/07/14)
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- Anti-AIDS agents 81. design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors
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In our continuing study of triterpene derivatives as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3′ dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor, which is currently in phase IIb clinical trials. In addition, another triterpene skeleton, moronic acid (MA, 3), was also employed to study the influence of the backbone and the C-3 modification toward the anti-HIV activity of this compound class. This study enabled us to better understand the structure-activity relationships (SAR) of triterpene-derived anti-HIV agents and led to the design and synthesis of compound 12 (EC50: 0.0006 μM), which displayed slightly better activity than 2 as a HIV-1 maturation inhibitor.
- Qian, Keduo,Kuo, Reen-Yun,Chen, Chin-Ho,Huang, Li,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
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experimental part
p. 3133 - 3141
(2010/09/18)
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- Toward the synthesis of didemnaketal B: A convergent synthesis of the C9-C28 subunit
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(Chemical Equation Presented) Synthesis of the C9-C28 subunit of didemnaketal B has been developed. This subunit was convergently prepared from four chiral synthons and at the longest linear sequence required 16 steps.
- Ito, Hisanaka,Inoue, Takaya,Iguchi, Kazuo
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supporting information; experimental part
p. 3873 - 3876
(2009/07/09)
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- Enantioselective total synthesis of bistramide A
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The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments. Copyright
- Crimmins, Michael T.,DeBaillie, Amy C.
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p. 4936 - 4937
(2007/10/03)
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- Convergent synthesis of the putative biogenetic precursor of mycaperoxide B and a norsesterterpene triene isolated from an Australian sponge
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The synthesis of enantiomerically pure norsesterterpene triene ester 1, extracted from an Australian marine sponge Latrunculia brevis, has been achieved by preparation of E,E-diene 3a via a Julia one-pot olefination and addition to 2,5,5,8a-tetramethyl-oc
- Drew,Harwood,Jahans,Robertson,Swallow
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p. 185 - 188
(2007/10/03)
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- Synthesis of optically active diastereomers of a nonproteic neurotrophic mimetic
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The four diastereomers 3, elongated analogues of perhydroretinol, are synthesized starting from both optically pure 3-bromo-2-methyl-1-propanol enantiomers. All exhibit neurotrophic activity on cultured neuronal cells derived from fetal rat cerebral hemispheres.
- Keyling-Bilger, Florence,Schmitt, Gaby,Beck, Alain,Luu, Bang
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p. 14891 - 14904
(2007/10/03)
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