Synthesis, crystal, computational study and in vitro anti-tuberculosis activity of N-(furan-2-yl-methyl)-N-(phenyl(quinolin-3-yl)methyl) acetamide derivatives

Bai, Yan; Wang, Limin; Chen, Yu; Liu, Yuan; Xü, Wei; Sun, Tiemin

doi:10.1016/j.molstruc.2011.08.033

Cited by 3 publications

(3 citation statements)

References 41 publications

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“…The target compounds 1 and 2 were synthesized starting from racemic 6‐bromo‐3‐(chloro(phenyl)methyl)‐2‐methoxyquinolin (Scheme ) . (S)‐(−)‐1‐(1‐naphthyl)ethylamine was introduced as a chiral template, and a mixture of diastereomers ( A , B ) may be generated.…”

Section: Resultsmentioning

confidence: 99%

“…It was also reported that some mefloquine‐based compounds were identified with relatively potent activity against nonreplicating persistent TB, and a remarkable similarity of mefloquine to bedaquiline was found when it was superimposed with bedaquiline replaced hydroxyl group with C–N double bond, and obtained derivative I displaying a better than or equal anti‐TB activity to that of mefloquine . Based on this, some efforts have been made by our group to develop anti‐TB drugs based on structure activity relationship of bedaquiline . Our group replaced the hydroxyl group of bedaquiline with acid amide (Scheme ) considering that the acid amide may fill the same role as hydroxyl group after acid amide–enol tautomerization.…”

Section: Introductionmentioning

confidence: 83%

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Design, Synthesis, Configuration Research, and In Vitro Antituberculosis Activities of two Chiral Naphthylamine Substituted Analogs of Bedaquiline

Wang

Zhou

et al. 2016

Journal of Heterocyclic Chem

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Two chiral naphthylamine‐substituted analogs of Bedaquiline were selected from a series of compounds designed as anti‐tuberculosis drugs based on the structure activity relationship of bedaquiline for synthetic and stereochemical research. The compounds were synthesized from the chiral precursors for the first time, and their absolute configurations were determined by electronic circular dichroism and quantum chemical calculations. Conformational analyses were performed on the compounds to find the stable conformers and get better predicted results. In addition, the in vitro antituberculosis activities of the two compounds were investigated.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 83%

Design, Synthesis, Configuration Research, and In Vitro Antituberculosis Activities of two Chiral Naphthylamine Substituted Analogs of Bedaquiline

Wang

Zhou

et al. 2016

Journal of Heterocyclic Chem

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“…In mefloquine-based compounds, the derivative 1 demonstrated better or equal anti-TB activity to that of mefloquine. Our group has focused on the development of potent anti-tuberculosis drugs [21,22,23,24], and in our preciously studies, we have designed and synthesized bedaquiline analogies which possessed similar spatial molecular structures as bedaquiline. However, in the case of anti-tubercular activity studies, although most compounds demonstrated biological activity, the unsatisfactory result was that all showed lower inhibitory activities than the standard drugs.…”

Section: Introductionmentioning

confidence: 99%

Design and Stereochemical Research (DFT, ECD and Crystal Structure) of Novel Bedaquiline Analogs as Potent Antituberculosis Agents

Geng

et al. 2016

Molecules

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A series of bedaquiline analogs containing H-bond donors were designed as anti-Mycobacterium tuberculosis drugs. A pair of diastereoisomers (R/S-and S/S-isomers) was selected from these designed compounds for synthetic and stereochemical research. The title compounds were synthesized from chiral precursors for the first time and the absolute configurations (ACs) were determined by electronic circular dichroism (ECD) with quantum chemical calculations. Moreover, a single crystal of the S/S compound was obtained for X-ray diffraction analysis, and the crystal structure showed high consistency with the geometry, confirming the reliability of ACs obtained by ECD analyses and theoretical simulation. Furthermore, the effect of stereochemistry on the anti-tuberculosis activity was investigated. The MICs of the R/S-and S/S-isomers against Mycobacterium phlei 1180 are 9.6 and 32.1 µg¨mL´1, respectively. Finally, molecular docking was carried out to evaluate the inhibitory nature and binding mode differences between diastereoisomers.

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Determination of Absolute Configurations of Bedaquiline Analogs by Quantum Chemical Electronic Circular Dichroism Calculations and an X‐ray Diffraction Study

Wang¹,

Zhao²,

Chen³

et al. 2014

Eur J Org Chem

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Two chiral analogs of bedaquiline were selected from a series of compounds designed as anti‐Mycobacterium tuberculosis drugs for synthetic and stereochemical research. The compounds were synthesized from chiral precursors for the first time, and the absolute configurations (ACs) were determined by electronic circular dichroism (ECD) and quantum chemical calculations. Single crystals of both compounds were obtained for X‐ray analysis, and the crystal structures and ab initio calculated geometries were extremely similar, which permitted a comparison of the relative reliabilities of ACs obtained by ECD analyses and theoretical simulation. In addition, the in vitro antituberculosis activities of the two compounds were investigated.

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Synthesis, crystal, computational study and in vitro anti-tuberculosis activity of N-(furan-2-yl-methyl)-N-(phenyl(quinolin-3-yl)methyl) acetamide derivatives

Cited by 3 publications

References 41 publications

Design, Synthesis, Configuration Research, and In Vitro Antituberculosis Activities of two Chiral Naphthylamine Substituted Analogs of Bedaquiline

Design, Synthesis, Configuration Research, and In Vitro Antituberculosis Activities of two Chiral Naphthylamine Substituted Analogs of Bedaquiline

Design and Stereochemical Research (DFT, ECD and Crystal Structure) of Novel Bedaquiline Analogs as Potent Antituberculosis Agents

Determination of Absolute Configurations of Bedaquiline Analogs by Quantum Chemical Electronic Circular Dichroism Calculations and an X‐ray Diffraction Study

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