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Lower homologues of okoumal and disila-okoumal: Synthesis and olfactory characterization of novel ambergris odorants

(Chemical Equation Presented) A structure-odor relationship study on lower homologues of the ambergris odorant okoumal with an El-CH2-El (3: El=C; 4: El=Si) or El-O-El moiety (5: El=Si) was carried out. All four stereoisomers of 3-5 were synthesized and characterized by odor descriptions and detection thresholds. The lowest odor thresholds were measured for the 2R configured isomers, with the 2R,4R configured 4a (El=Si, X=CH2) being the most intense of the series and best also with respect to its odor character.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The asymmetric hydration of 1-octene to (S)-(+)-2-octanol with a biopolymer-metal complex, silica-supported chitosan-cobalt complex

A new biopolymer-non-noble metal catalyst, silica-supported chitosan-cobalt complex (SiO2-CS-Co), has been prepared by a simple method and found to be a high stereoselective catalyst for asymmetric hydration of 1-octene to (S)-(+)-2-octanol amounted to 97.8%ee when fitting conditions were selected. This catalyst was very stable and could be reused several times without any remarkable change in catalytic activity and optical selectivity. Obviously, the present work has provided a more economical alternative way for the preparation of a chiral 2-octanol.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Efficient total synthesis of iso-cladospolide B and cladospolide B

An efficient synthesis of iso-cladospolide B and cladospolide B has been achieved using Jacobsen’s hydrolytic kinetic resolution (HKR), Sharpless asymmetric dihydroxylation and Yamaguchi macrolactonization as the key steps.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Induction of a preferred twist in a biphenyl core by stereogenic centers: A novel approach to the absolute configuration of 1,2- and 1,3-diols

A quick, simple, and reliable method to assign the absolute configuration of 1,2- and 1,3-diols: all that is needed is to measure the CD sign of the A band (250 nm) of their biphenyldioxolanes 1 (n = 0,1). The chirality of the diol induces a preferred sense of twist in the biphenyl moiety (R,R-M and S,S-P), and a positive A band (a probe of M twist) reveals an R or R,R configuration of the diol.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Synthesis and antiretroviral evaluation of new alkoxy and aryloxy phosphate derivatives of 3′-azido-3′-deoxythymidine

A series of new ether lipid-3′-azido-3′-deoxythymidine (AZT) conjugates (11a-g) were synthesized and evaluated for anti-HIV activity. The effect of chirality on the antiviral activity was examined through the synthesis of AZT conjugates bearing alkoxypropanols in the lipid portion of the molecule (11a-d). In addition, the long alkyl chain of alkoxyethyl ether lipid-AZT analogs was replaced with aromatic groups (11e-g), and the effect of this structural modification on activity is reported. The results of the biological tests indicate that analogs with a methyl group alpha to the phosphate moiety (11c,d) exhibit a marked degree of stereoselectivity with regard to their anti-HIV activity. Also, replacement of the long alkyl chain with aromatic groups in the oxyalkyl ether phospholipid-AZT conjugates leads to substantially more potent compounds (11e-g) with an anti-HIV activity comparable to that of AZT.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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COMBINATION THERAPY FOR TREATING CYCLOOXYGENASE-2 MEDIATED DISEASES OR CONDITIONS IN PATIENTS AT RISK OF THROMBOTIC CARDIOVASCULAR EVENTS

The invention is directed to a method for treating a cyclooxygenase-2 mediated disease or condition in a mammalian patient at risk of a thrombotic cardiovascular event, wherein the patient is on aspirin therapy to reduce the risk of the thrombotic cardiovascular event, comprising orally concomitantly or sequentially administering to the patient a cyclooxygenase-2 selective inhibitor in an amount effective to treat the cyclooxygenase-2 mediate disease or condition, and a nitric oxide donating compound in accordance with Formula (I) or a pharmaceutically acceptable salt thereof, wherein the nitric oxide donating compound is administered in an amount effective to reduce the gastrointestinal toxicity caused by the combination of the cyclooxygenase-2 selective inhibitor and aspirin. Pharmaceutical compositions are also encompassed.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Indolyl Azaspiroketal Mannich Bases Are Potent Antimycobacterial Agents with Selective Membrane Permeabilizing Effects and in Vivo Activity

The inclusion of an azaspiroketal Mannich base in the membrane targeting antitubercular 6-methoxy-1-n-octyl-1H-indole scaffold resulted in analogs with improved selectivity and submicromolar activity against Mycobacterium tuberculosis H37Rv. The potency enhancing properties of the spiro-fused ring motif was affirmed by SAR and validated in a mouse model of tuberculosis. As expected for membrane inserting agents, the indolyl azaspiroketal Mannich bases perturbed phospholipid vesicles, permeabilized bacterial cells, and induced the mycobacterial cell envelope stress reporter promoter piniBAC. Surprisingly, their membrane disruptive effects did not appear to be associated with bacterial membrane depolarization. This profile was not uniquely associated with azaspiroketal Mannich bases but was characteristic of indolyl Mannich bases as a class. Whereas resistant mycobacteria could not be isolated for a less potent indolyl Mannich base, the more potent azaspiroketal analog displayed low spontaneous resistance mutation frequency of 10-8/CFU. This may indicate involvement of an additional envelope-related target in its mechanism of action.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Thiolates chemically induce redox activation of BTZ043 and related potent nitroaromatic anti-tuberculosis agents

The development of multidrug resistant (MDR) and extensively drug resistant (XDR) forms of tuberculosis (TB) has stimulated research efforts globally to expand the new drug pipeline. Nitroaromatic compounds, including 1,3-benzothiazin-4-ones (BTZs) and related agents, are a promising new class for the treatment of TB. Research has shown that the nitroso intermediates of BTZs that are generated in vivo cause suicide inhibition of decaprenylphosphoryl- beta-d-ribose 2? oxidase (DprE1), which is responsible for cell wall arabinogalactan biosynthesis. We have designed and synthesized novel anti-TB agents inspired from BTZs and other nitroaromatic compounds. Computational studies indicated that the unsubstituted aromatic carbons of BTZ043 and related nitroaromatic compounds are the most electron-deficient and might be prone to nucleophilic attack. Our chemical studies on BTZ043 and the additional nitroaromatic compounds synthesized by us and others confirmed the postulated reactivity. The results indicate that nucleophiles such as thiolates, cyanide, and hydride induce nonenzymatic reduction of the nitro groups present in these compounds to the corresponding nitroso intermediates by addition at the unsubstituted electron-deficient aromatic carbon present in these compounds. Furthermore, we demonstrate here that these compounds are good candidates for the classical von Richter reaction. These chemical studies offer an alternate hypothesis for the mechanism of action of nitroaromatic anti-TB agents, in that the cysteine thiol(ate) or a hydride source at the active site of DprE1 may trigger the reduction of the nitro groups in a manner similar to the von Richter reaction to the nitroso intermediates, to initiate the inhibition of DprE1.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A (S)- propylene carbonate synthesis method (by machine translation)

The present invention provides a (S)- propylene carbonate synthesis method, comprises a batch charging, temperature reaction, cooling, decompression desolution of the reaction. The invention preparation of (S)- propylene carbonate, yield is 97%; the invention preparation of (S)- propylene carbonate, the specific optical rotation is – 2 – – 3; chemical pure content ? 99.8%; optical pure content ? 99.4%; isomer content ? 0.6%; water content ? 0.1%; the appearance is a colorless clear transparent liquid; from feeding to prepare crude product, the reaction time is 25 hours. (by machine translation)

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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A stereoselective synthesis of dinucleotide phosphorothioate triesters through a chiral indol-oxazaphosphorine intermediate

(S)-1-(indol-2-yl)-propan-2-ol was used as a chiral auxiliary to form a dinucleotide phosphorothioate triester in 97% ee.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate