re- andsi-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt: A Highly Stereoselective Synthesis of the HIV Protease Inhibitor Amprenavir (Vertex 478)

Corey, E. J.; Zhang, Fuyao

doi:10.1002/(sici)1521-3773(19990712)38:13/14<1931::aid-anie1931>3.0.co;2-4

Cited by 289 publications

(94 citation statements)

References 4 publications

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“…14 Warfarin has supporting impact on rosuvastatin. 29 Erythromycin 30 and finofibrate 31 have not shown interaction. Some protease inhibitors also interact with rosuvastatin.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of Metal Complexes of Rosuvastatin

Tabassum¹,

Arayne²,

Sultana³

2017

IJPER

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Context: Rosuvastatin is a cholesterol lowering drug. It belongs to class statin. It is prescribed to the patients of coronary artery disease; atherosclerosis; thrombosis; increased low-density-lipoprotein; lipid and triglyceride. Aims:It is a newer drug in market and studies over the pharmacodynamics and pharmacokinetics are in progress. Statin therapy is a long term treatment for which its behavior in the presence of other agents is necessary. For this purpose present study is based on the interaction of the drug with essential and trace elements present in human body or co-administered during multivitamin therapy. Settings and Design: Complexes of rosuvastatin with Cd(II), Cr(II), Mn(II), Fe(III), Co(II), Ni(II) and Zn(II) i.e., metals commonly present in multivitamins, were synthesized in laboratory. Methanolic solution of rosuvastatin with metal chloride salts was reacted. Methods and Material: Reaction between drug and metals was carried out in thermostat at 80 o C for five hours with timely TLC monitoring for completion of reaction. These newly synthesized complexes were identified by IR and NMR spectroscopy and CHN elemental microanalysis and the structure of complexes was proposed. Results: Analyses suggest two molecules of rosuvastatin co-ordinate with the central metal atom through their carboxylic group. CS Chem3D ultra suggests square planner structure of the complex. Conclusions: Synthesis of compounds proposes that rosuvastatin can bind to metals as ligand through its pharmocophore site that may lead to reduced activity of drug and metal both. The study is precursor to in vitro and in vivo study of interaction of drug and metals.

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“…14 Warfarin has supporting impact on rosuvastatin. 29 Erythromycin 30 and finofibrate 31 have not shown interaction. Some protease inhibitors also interact with rosuvastatin.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of Metal Complexes of Rosuvastatin

Tabassum¹,

Arayne²,

Sultana³

2017

IJPER

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“…Corey and colleagues applied their catalyst to the asymmetric Henry (nitro aldol) reaction using chiral aminoaldehydes and the short-step synthesis of an HIV protease inhibitor (Scheme 3.9) [26]. Interestingly, a newly generated asymmetric center is controlled by the chiral catalyst and nitrogen substituents.…”

Section: Asymmetric Aldol Reactionmentioning

confidence: 99%

Cinchona‐Derived Chiral Phase‐Transfer Catalysts for Other Asymmetric Synthesis

Arai

2008

Asymmetric Phase Transfer Catalysis

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Phase-transfer catalysis has been recognized as one of the most powerful synthetic tools for establishing practical protocols because it offers several advantages, such as operational simplicity, mild conditions with aqueous media, suitability for large-scale reaction, and an environmentally benign nature. Since the pioneering studies on asymmetric alkylation promoted by chiral phase-transfer catalysts (PTCs) [1,2], this research area has served as an attractive area for the pursuit of green chemistry, and many types of chiral quaternary ammonium salts for various asymmetric phasetransfer catalyses have been developed over the past few decades [3,4]. For example, two-center organocatalysis using bis-ammonium salts derived from tartrate represents a new concept in asymmetric PTC chemistry [5].In particular, it is not only the cinchona alkaloids that are suitable chiral sources for asymmetric organocatalysis [6], but also the corresponding ammonium salts. Indeed, the latter are particularly useful for chiral PTCs because: (1) both pseudo enantiomers of the starting amines are inexpensive and available commercially; (2) various quaternary ammonium salts can be easily prepared by the use of alkyl halides in a single step; and (3) the olefin and hydroxyl functions are beneficial for further modification of the catalyst. In this chapter, the details of recent progress on asymmetric phase-transfer catalysis are described, with special focus on cinchonaderived ammonium salts, except for asymmetric alkylation in a-amino acid synthesis. Asymmetric Darzens ReactionThe Darzens reaction is a fundamental reaction, the products of which are extremely useful for the synthesis of other molecules. Despite these advantages, the reaction Asymmetric Phase Transfer Catalysis. Edited by Keiji Maruoka

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Section: Introductionmentioning

confidence: 99%

“…β-blockers), unnatural β-amino acids, pesticides and chiral auxiliaries. [29][30][31][32] Additionally, β-amino alcohols have many applications as antibiotics, anti-bacterial drugs and, steroids.33 One of the most classical approaches toward the synthesis of β-amino alcohols is the direct ring opening by amines of epoxides. The existing protocols of β-amino alcohols have been achieved by ring opening of epoxides with simple amines (aromatic/ aliphatic) in the presence of various catalysts including metals such as Cu, 34,35 Fe,30,36,37 55 These protocols were significant, however, some of them have some drawbacks including the use of expensive chemicals, air and moisture sensitive reagents or catalysts, high pressures, inert atmospheric conditions, the requirement for protracted work-up procedures and so on.…”

mentioning

confidence: 99%

Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol‑Based β-Amino Alcohol Derivatives

Manda

Prasad

Thatikonda

et al. 2017

J. Braz. Chem. Soc.

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The synthesis of novel amino alcohol derivatives based on cardanol and glycerol were achieved in good yields and characterized by 1 H and 13 C NMR (nuclear magnetic resonance) and MS (mass spectrometry). In addition, we evaluated the in vitro antimicrobial activity against Gram-positive (Staphylococcus aureus, standard and clinical strains), Gram-negative (Escherichia coli) and M. tuberculosis bacterial strains. The bioassay results indicated that four compounds showed activity against S. aureus, including the clinical resistant strain, with MIC (minimum inhibitory concentration) ranging from 3.90 to 15.60 µg mL -1 and M. tuberculosis, with MIC 90 (minimum inhibitory concentration required to inhibit the growth of 90% of organisms) ranging from 3.18 to 7.36 µg mL -1 .Keywords: CNSL, cardanol, amino alcohols, epoxide ring opening, antimicrobial activity IntroductionThe synthesis of fine chemicals from natural renewable resources has received great interest in synthetic community and is becoming a significant and challenging theme for researchers of both the academic and industrial sectors. Among the renewable materials, cardanol has attracted considerable attention due to its unique nature.1 Cardanol is a low cost, naturally occurring renewable non-isoprenoic phenolic lipid-mixture of cashew nut shell liquid (CNSL). The structural benefits of cardanol are carrying reactive phenolic group and hydrophobic alkyl/alkenyl side chain at meta-position of phenolic group. With these unique structural features, cardanol and its derivatives are renowned amphiphilic building blocks and precursors of high-value fine chemicals and supramolecular structures. Its derivatives present many biological activities such as: fungicidal, bactericidal, molluscicidal, larvicidal, anti-inflammatory, antioxidant and, towards serious disorders like cancer and obesity. [2][3][4][5][6][7][8][9] It is also described in the literature in recent years, that cardanol frameworks are involved to build phenolic resins, 10-12 bio-based polymers, 13 epoxy curing resins, 14-16 reactive diluents, 17,18 and fluorescent compounds. 19,20 Similarly, glycerol is another important renewable material used in the synthesis of higher value-added fine chemicals through green chemistry procedures in the last years. It may be applied, for instance, to generate hydrogen gas, 21 Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol-Based β-Amino Alcohol Derivatives J. Braz. Chem. Soc. 640 Cardanol and glycerol can be starting materials to prepare β-amino alcohols which is a vital interesting class of organic intermediates due to their abundant existence in nature and they are useful in the preparation of wide range of biologically active natural and synthetic frameworks, pharmaceuticals (e.g. β-blockers), unnatural β-amino acids, pesticides and chiral auxiliaries. [29][30][31][32] Additionally, β-amino alcohols have many applications as antibiotics, anti-bacterial drugs and, steroids.33 One of the most classical approaches toward the syn...

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re- andsi-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt: A Highly Stereoselective Synthesis of the HIV Protease Inhibitor Amprenavir (Vertex 478)

Cited by 289 publications

References 4 publications

Synthesis and Spectroscopic Characterization of Metal Complexes of Rosuvastatin

Synthesis and Spectroscopic Characterization of Metal Complexes of Rosuvastatin

Cinchona‐Derived Chiral Phase‐Transfer Catalysts for Other Asymmetric Synthesis

Synthesis, Antibacterial and Antitubercular Evaluation of Cardanol and Glycerol‑Based β-Amino Alcohol Derivatives

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