110567-21-0Relevant articles and documents
PCSK9 INHIBITORS AND METHODS OF USE THEREOF
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Page/Page column 146-147, (2020/07/31)
The invention relates to a novel inhibitor pharmacophore of PCSK9 and heteroaryl compounds that bind the PCSK9 protein.
PCSK9 INHIBITORS AND METHODS OF USE THEREOF
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Page/Page column 145-146, (2020/07/31)
The invention relates to novel heteroaryl compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cardiovascular diseases, and methods treating sepsis or septic shock, using the novel heterocyclic compounds disclosed herein.
STING MODULATOR COMPOUNDS, AND METHODS OF MAKING AND USING
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Paragraph 0216, (2019/05/30)
The present disclosure provides STING modulators/agonists, and methods of synthesis and methods for using for the prophylaxis or treatment of cancer and other STING-related diseases. The present disclosure relates to a compound represented by the Formula (I): wherein each symbol is as defined in the description, or a pharmaceutically acceptable salt thereof.
Preparation method of optical pure cyclopentene alcohol serving as medical intermediate
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, (2017/10/09)
The invention relates to a preparation method of optical pure cyclopentene alcohol serving as a medical intermediate. The preparation method comprises the following steps: by taking 3-butenal and a 3-bit or 4-bit derivative thereof as raw materials, synthesizing an optical pure hydroxyaldehyde condensation product under the existence of a catalytic amount of (S)-proline, reducing an aldehyde group into a hydroxyl group, protecting the hydroxyl group with benzyl bromide, and performing efficient double-bond translocation closed loop reaction, thus obtaining (1S, 2R)-2-benzoxymethylcyclopentyl-3-alkene-1-alcohol. According to the method provided by the invention, reaction conditions are mild, the raw materials and reagents are low in cost and readily available, the yield is high, and the method is suitable for industrial production.
The synthesis of possible transition state analogue inhibitors of thymidine phosphorylase
Evans, Gary B.,Gainsford, Graeme J.,Schramm, Vern L.,Tyler, Peter C.
, p. 406 - 409 (2015/04/27)
The synthetically challenging SN2 transition state mimic for thymidine phosphorylase, along with its phosphonate analogue, were synthesised via a modified Corey-Link reaction in good overall yields and ensuring the correct stereochemical outcome.
N-O bond as a glycosidic-bond surrogate: Synthetic studies toward polyhydroxylated N-alkoxypiperidines
Malik, Ga?lle,Ferry, Angélique,Guinchard, Xavier,Cresteil, Thierry,Crich, David
supporting information, p. 2168 - 2179 (2013/03/29)
A series of novel polyhydroxylated N-alkoxypiperidines has been synthesized by ring-closing double reductive amination (DRA) of highly functionalized 1,5-dialdehydes with various hydroxylamines. The required saccharide-based dialdehydes were prepared efficiently from sodium cyclopentadienylide in seven steps. A two-step protocol has been developed for the DRA; it led, after deprotection, to isofagomine, 3-deoxyisofagomine, and numerous other N-alkoxy analogues. The barrier to inversion in these polyhydroxylated N-alkoxypiperidine derivatives was found by variable-temperature NMR methods to be approximately 15 kcal mol-1. With the exception of N-hydroxyisofagomine itself, none of the compounds prepared showed significant inhibitory activity against sweet almond β-glucosidase. Copyright
Asymmetric synthesis of polyhydroxylated N -alkoxypiperidines by ring-closing double reductive amination: Facile preparation of isofagomine and analogues
Malik, Gaelle,Guinchard, Xavier,Crich, David
supporting information; scheme or table, p. 596 - 599 (2012/02/16)
A de novo synthesis of novel polyhydroxylated N-alkoxypiperidines based on the ring-closing double reductive amination of 1,5-dialdehydes, obtained by oxidative cleavage of cyclopentene derivatives, with O-substituted hydroxylamines is reported. Isofagomine was accessed by cleavage of the N-O bond of an N-alkoxypiperidine.
Properties of oligonucleotide with phenyl-substituted carbocyclic nucleoside analogs for the formation of duplex and triplex DNA
Nasr, Tamer,Taniguchi, Yosuke,Takaki, Tomoko,Okamura, Hidenori,Sasaki, Shigeki
, p. 841 - 860 (2013/02/23)
(1S,3S,4R)-1-Phenyl-1-thymidyl-3-hydroxy-4-hydroxymethylcyclopentane (10) and their analogs were synthesized, incorporated into the oligodeoxynucleotides, and their properties were evaluated for the formation of duplex and triplex DNA. The known chiral cyclopentanone derivative was converted into the corresponding ketimine sulfonamide derivative, which was subjected to a stereoselective PhLi addition. The formed sulfonamide was hydrolyzed to afford the primary amino group, on which the thymine moiety was built. The benzyl protecting groups were removed to form the nucleoside analog having a phenyl group and the thymine unit at the 1 position of a carbocyclic skeleton (10). In the estimation of the oligodeoxynucleotides incorporating 10 for duplex and triplex formation, the carbocyclic nucleoside analog 10 did not show the stabilizing effect for duplex formation; on the other hand, it stabilized the triplex. Therefore, the skeleton of the phenyl-substituted carbocyclic nucleoside analog 10 may be a platform for the formation of stable triplex DNA.
Synthesis of [13C4]Baraclude (entecavir)
Tran, Scott B.,Ekhato, Ihoezo V.,Rinehart, J. Kent
scheme or table, p. 485 - 489 (2010/07/04)
Entecavir, labeled as 1H-[13C4]purin-6(9H)-one, was prepared from commercially available [13C]guanidine HCl, 1 and diethyl [1,2,3-13C3]malonate, 2. The reagents were condensed together to give 2-amino-4,6-dichloro[2,4,5,6-13C 4]pyrimidine 3, which in turn was coupled to an optically active amino cyclopentanol derivative, 9. A further sequence of eight reaction steps completed the constructions of the purine ring system and the exocyclic olefin attachment on the cyclic pentyl portion, 18. The removal of the methoxide and benzyl protecting groups gave [13C4]entecavir, 20 in an overall yield of 6.8%. The chemical purity of the title compound was determined by HPLC to be 99.23%. The percent isotopic [13C4] abundance was found by mass spectral analysis to be 96.7%. No detectable level of the unlabeled entecavir was found by LC-MS analysis. Copyright
Novel 3′-deoxy analogs of the anti-HBV agent entecavir: Synthesis of enantiomers from a single chiral epoxide
Ruediger, Edward,Martel, Alain,Meanwell, Nicholas,Solomon, Carola,Turmel, Brigitte
, p. 739 - 742 (2007/10/03)
A synthesis of novel 3′-deoxy analogs of the anti-HBV agent entecavir (BMS-200475) was devised using regioselective ring opening of suitable cyclopentene epoxides as the key step. This versatile approach afforded access to an enantiomeric pair of carbocyclic nucleosides from a single chiral intermediate.
