Enantioselective Synthesis of ((1<i>R</i>,2<i>R</i>)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate

Ganesh, K. Ravi; Pachore, Sharad S.; Pratap, T. V.; Umesh, K.; Rao, Mandava V. Basaveswara; Murthy, C. N.; Babu, M. Suresh

doi:10.1080/00397911.2015.1074695

Cited by 5 publications

(3 citation statements)

References 9 publications

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“…Through a series of comprehensive investigations, we synthesized a chiral ligand (1 R ,2 R )-2-(pyridin-4-ylcarbamoyl) cyclohexanecarboxylic acid (RR-PCCHC) from (1 R ,2 R )-cyclohexane-1,2-dicarboxylic acid as starting materials. First, (1 R ,2 R )-cyclohexane-1,2-dicarboxylic acid is a cheap and easy-to-get material; second, 1,2-substituted cyclohexane derivatives are an important part of many biologically active compounds including alkaloids, pharmaceuticals, and research probes . Meanwhile, the formation of amide bond by a condensation reaction of cyclohexane acid and pyridin-4-amine could provide the N- and O-group receptor of the hydrogen bond with amino acids.…”

Section: Introductionmentioning

confidence: 99%

“…First, (1R,2R)-cyclohexane-1,2-dicarboxylic acid is a cheap and easy-to-get material; second, 1,2-substituted cyclohexane derivatives are an important part of many biologically active compounds including alkaloids, pharmaceuticals, and research probes. 57 Meanwhile, the formation of amide bond by a condensation reaction of cyclohexane acid and pyridin-4-amine could provide the N-and O-group receptor of the hydrogen bond with amino acids. We report herein a homochiral MOF [Zn(RR-PCCHC) 2 ] (HMOF-1) which shows 2D layered structure constructed by DNA-like righthanded double helical motifs.…”

Section: ■ Introductionmentioning

confidence: 99%

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Homochiral MOF as Circular Dichroism Sensor for Enantioselective Recognition on Nature and Chirality of Unmodified Amino Acids

Zhao

Wang

Zhang

2017

ACS Appl. Mater. Interfaces

105

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Self-assembly of zinc salt with rationally designed chiral ligand, (1R,2R)-2-(pyridine-4-ylcarbamoyl) cyclohexanecarboxylic acid (RR-PCCHC) generated 2D homochiral metal-organic framework [Zn(RR-PCCHC)] (HMOF-1) that is composed of DNA-like right-handed double-helix structure. HMOF-1 shows high solvent and thermal stability and is also stable in neutral, weak acidic and weak basic aqueous solution. Emulsified HMOF-1 shows strong inherent circular dichroism (CD) signal in aqueous solution, which can show regular intensity change by induction of amino acids. On the basis of the measuring of CD signal intensity, a chemosensor for unmodified amino acids is fabricated, which differ from reported those in which CD signal is amplified by a complicated chemical reaction of originally CD-silent molecule with probed amino acids. This chemosensor can be used for rapid, convenient and sensitive detection of micro amount of amino acids. Most remarkably, 3 × 10 mol of l-aspartic acid and 4 × 10 mol of d-aspartic acid in aqueous solution can completely quench CD signal of emulsified HMOF-1 in HO. It is found that the difference of recognition ability between d- and l-proline is the largest in all probed amino acids. The LOD (limit of detection) of the proposed sensor for the determination of aspartic acid is 13.31 ppm. The recognition efficiency η = [Formula: see text] × 100% for l-aspartic acid is as high as 92.1%. The interacting mechanism of DNA-like HMOF-1 with probed amino acids is similar to that of groove binding of targeting drug with DNA.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Homochiral MOF as Circular Dichroism Sensor for Enantioselective Recognition on Nature and Chirality of Unmodified Amino Acids

Zhao

Wang

Zhang

2017

ACS Appl. Mater. Interfaces

105

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“…As demonstrated in Scheme , we initially examined the dialkylation reaction between commercially available chiral compound 2 and 2,2′-biindole 1 . After optimizing the conditions (see Supporting Information Table S1 for more details), compound 3 was obtained in decagrams and 80% yield.…”

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confidence: 99%

Design and Synthesis of Diphosphine Ligands Based on the Chiral Biindolyl Scaffold and Their Application in Transition-Metal Catalysis

Zhang,

Chen,

Zhang

2024

Org. Lett.

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An extremely concise, scalable, and stereoselective synthesis of a privileged chiral skeleton based on 2,2′-biindolyl and commercially available chiral building blocks has been developed. This novel skeleton allows for easy access to a range of bisphosphine ligands (decagram scale, up to 58% total yield, only three steps). The synthetic method is characterized by an efficient central-to-axial chirality transfer strategy. In particular, the superior performance of the ligands has been demonstrated in diverse reactions, including several asymmetric hydrogenations, asymmetric conjugate reductions, and cycloisomerization reactions, indicating a great potential for the application of the newly developed chiral backbones in further modifications and exploration of novel chiral ligands and catalysts.

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Separation and characterization of related substances of Lurasidone hydrochloride by LC-QTOF-MS techniques

Siddig,

Liu,

Abdulbagi

et al. 2024

Journal of Pharmaceutical and Biomedical Analysis

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Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate

Cited by 5 publications

References 9 publications

Homochiral MOF as Circular Dichroism Sensor for Enantioselective Recognition on Nature and Chirality of Unmodified Amino Acids

Homochiral MOF as Circular Dichroism Sensor for Enantioselective Recognition on Nature and Chirality of Unmodified Amino Acids

Design and Synthesis of Diphosphine Ligands Based on the Chiral Biindolyl Scaffold and Their Application in Transition-Metal Catalysis

Separation and characterization of related substances of Lurasidone hydrochloride by LC-QTOF-MS techniques

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