35079-19-7Relevant academic research and scientific papers
Synthesis of L-2-(2-carboxy-4-methylenecyclopentyl)glycines (CPGs). Novel conformationally restricted glutamate analogues
Raghavan,Ishida, Michiko,Shinozaki, Haruhiko,Nakanishi, Koji,Ohfune, Yasufumi
, p. 5765 - 5768 (1993)
Three diastereomers 1, 2, and 4 of a new glutamate analogue incorporating a 5-membered ring were synthesized in a stereocontrolled manner. 1′R-Isomers 2 and 4 were constructed from the α,β-unsaturated 2,2,2-trifluoroethyl esters 5b and 10b by a [3+2] cycloaddition with a Pd-trimethylenemethane (TMM) complex. The 1′S isomer 1 was synthesized by a 1,4-addition of TMM equivalent to the α,β-unsaturated methyl ester 10a. The folded isomer 4 was characterized electrophysiologically to be a potent agonist of kainate receptors in the mammalian central nervous systems.
PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS
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Page/Page column 301-302, (2020/10/18)
This disclosure provides pharmaceutical compounds to treat medical disorders, such as complement-mediated disorders, including complement Cl -mediated disorders.
COMPOUNDS FOR TREATMENT OF IMMUNE AND INFLAMMATORY DISORDERS
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Paragraph 0790, (2017/03/14)
Compounds, methods of use, and processes for making inhibitors of complement Factor D are provided comprising Formula I, I" and I'" or a pharmaceutically acceptable salt or composition thereof. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade. The inhibitors of Factor D described herein reduces the excessive activation of complement.
PROCESSES AND INTERMEDIATES FOR PREPARING A MACROCYCLIC PROTEASE INHIBITOR OF HCV
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Page/Page column 22; 32, (2017/01/09)
Disclosed is a process for the preparation of certain intermediates, e.g. those in the scheme below: which intermediates and processes are useful in the preparation of the macrocyclic HVC inhibitor Simeprevir.
PROCESSES AND INTERMEDIATES FOR PREPARING A MACROCYCLIC PROTEASE INHIBITOR OF HCV
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, (2011/10/10)
A process for preparing [(1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, by the resolution of racemic 4-oxo-1,2-cyclopentanedicarboxylic acid (V), said process comprising: (a) reacting 4-oxo-1,2-cyclopentanedicarboxylic acid (V) with brucine or (1R,2S)-(-)- ephedrine, thus preparing the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of (V), and (b) precipitating selectively the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of (1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, while the bis-brucine or bis- (1R,2S)-(-)-ephedrine salt of [(1S,2S)-4-oxo-1,2-cyclopentanedicarboxylic acid stays in solution; (c) liberating the acid II by removal of brucine or (1R,2S)-(-)-ephedrine from the precipitated salt obtained in step (b).
Stereoselective total synthesis of (-)-borrelidin
Vong, Binh G.,Kim, Sun Hee,Abraham, Sunny,Theodorakis, Emmanuel A.
, p. 3947 - 3951 (2007/10/03)
A convergent synthesis of (-)-borrelidin (1) is reported based on the retrosynthetic disconnections indicated in the picture. Highlights of the strategy include the construction of a strained enynone-containing macrolide and the installation of a cyano group in a regioselective manner by a novel molybdenum-catalyzed hydrostannation of the alkyne.
The Synthesis of Novel Trans-Oxabicyclo[3,3,0]octane Systems as Potential Inhibitors of HIV Protease
Mahler, Mikael E.,Palmer, Michael J.
, p. 193 - 194 (2007/10/03)
The novel trans-3-oxabicyclo[3,3.0]octan-7-one system has been prepared by intramolecular ring closure of the corresponding cyclopentane diol. Peralkylation and benzylidene substitution of the octanone has allowed the preparation of tetra-alkylated potential inhibitors of HIV protease. Weak activity against HIV protease (IC50's 70-100μM) was observed.
Synthesis and pharmacological characterization of aminocyclopentanetricarboxylic acids: New tools to discriminate between metabotropic glutamate receptor subtypes
Acher, Francine C.,Tellier, Frédérique J.,Azerad, Robert,Brabet, Isabelle N.,Fagni, Laurent,Pin, Jean R.
, p. 3119 - 3129 (2007/10/03)
The four stereoisomers of 1-aminocyclopentane-1,3,4-tricarboxylic acid {ACPT-I (18) and -II (19), (3R,4R)-III [(-)-20], and (3S,4S)-III [(+)-20]} have been synthesized and evaluated for their effects at glutamate receptors subtypes. ACPTs are ACPD analogues in which a third carboxylic group has been added at position 4 in the cyclopentane ring. None of the ACPT isomers showed a significant effect on ionotropic NMDA, KA, and AMPA receptors. On the other hand, ACPT-III (19) was found to be a general competitive antagonist for metabotropic receptors (mGluRs) and exhibited a similar affinity for mGluR1a (K(B) = 115 ± 2 μM), mGluR2 (K(B) = 88 ± 21 μM), and mGluR4a (K(B) = 77 ± 9 μM), the representative members of group I, II and III mGluRs, respectively. Two other isomers, ACPT-I (18) and (+)-(3S,4S)-ACPT-III [(+)- 20], were potent agonist at the group III receptors mGluR4a (EC50 = 7.2 ± 2.3 and 8.8 ± 3.2 μM) and competitive antagonists with low affinity for mGluR1a and mGluR2 (K(B) > 300 μM). Finally, (-)-(3R,4R)-ACPT-III [(-)-20] was a competitive antagonist with poor but significant affinity for mGluR4a (K(B) = 220 μM). These results demonstrate that the addition of a third carboxylic group to ACPD can change its activity (from agonist to antagonist) and either increase or decrease its selectivity and/or affinity for the various mGluR subtypes.
SYNTHESIS OF RING-ENLARGED CYCLOBUT-A AND CYCLOBUT-G ANALOGUES AS HIV INHIBITORS. PART 4
Boumchita, Hassane,Legraverend, Michel,Bisagni, Emile
, p. 1785 - 1792 (2007/10/02)
Two ring-expanded analogues (compounds 13 and 14) of the anti-HIV agents Cyclobut-A and Cyclobut-G are described.They were synthesized from trans-3,4-bis(hydroxymethyl)cyclobutylamine which was obtained from threo-3,4-bis(methoxycarbonyl)hexane dioic acid.Neither compound (13,14) was able to provide protection to CEM cells against HIV-1-infection.
