Synthesis and evaluation of novel coumarin-oxime ethers as potential anti-tubercular agents: Their DNA cleavage ability and BSA interaction study

Reddy, D. Narasimha; Kongot, Manasa; Netalkar, Sandeep P.; Kurjogi, Mahantesh; Kumar, Rakesh; Avecilla, Fernando; Kumar, Amit

doi:10.1016/j.ejmech.2018.03.042

Cited by 70 publications

(36 citation statements)

References 56 publications

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“…The Supporting Information features 1) general procedures for the synthesis of all compounds and data analysis; 2) 1 H NMR and 13…”

Section: Supporting Informationmentioning

confidence: 99%

“…Small organic molecules able to bind DNA provide promises for anticancer activity due to alteration of the structure and function of the genetic material. Amongst a plethora of such binders [1][2][3][4][5][6][7][8], various oxime derivatives were found to show affinity towards DNA [9][10][11][12], whereas others were found to cleave DNA as metal-free artificial nucleases [13,14].…”

Section: Introductionmentioning

confidence: 99%

“…Based on our interest in the chemistry and biology of the oxime functionality [54][55][56][57], as well as in their DNA photolytic interaction upon UV irradiation [9][10][11]43] we have decided to investigate the behaviour of carefully designed O-carbamoyl derivatives of p-pyridine amidoxime, ethanone oxime and aldoxime (VI, VII, VIII, R 1 = p-pyridyl, Figure 1) as DNA photosensitizers. Based on our previous ex-Scheme 1: Synthesis of O-carbamoyl amidoximes (8)(9)(10)(11)(12)(13), ethanone oximes (15)(16)(17)(18)(19)(20) and aldoximes (22)(23)(24)(25)(26)(27). Oxime 1 or 14 or 21, Et 3 N (1.1 equiv), R-NCO (1.1-1.8 equiv), dry chloroform or tetrahydrofuran, Ar, 0 °C → rt or reflux, 19-97%.…”

Section: Introductionmentioning

confidence: 99%

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p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

Gritzapis

Varras

Andreou

et al. 2020

Beilstein J. Org. Chem.

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A number of p-pyridinyl oxime carbamate derivatives were prepared upon the reaction of the corresponding oximes with isocyanates. These novel compounds reacted photochemically in the presence of supercoiled plasmid DNA. Structure–activity relationship (SAR) studies revealed that the substituent on the imine group was not affecting the extend of the DNA damage, whereas the substituent of the carbamate group was critical, with the halogenated derivatives to be able to cause extensive single and double stranded DNA cleavages, acting as “synthetic nucleases”, independently of oxygen and pH. Calf thymus–DNA affinity studies showed a good-to-excellent affinity of selected both active and non-active derivatives. Preliminary theoretical studies were performed, in an effort to explain the reasons why some derivatives cause photocleavage and some others not, which were experimentally verified using triplet state activators and quenchers. These theoretical studies seem to allow the prediction of the activity of derivatives able to pass intersystem crossing to their triplet energy state and thus create radicals able to damage DNA. With this study, it is shown that oxime carbamate derivatives have the potential to act as novel effective photobase generating DNA-photocleavers, and are proposed as new leads for “on demand” biotechnological applications in drug discovery and medicine.

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“…The Supporting Information features 1) general procedures for the synthesis of all compounds and data analysis; 2) 1 H NMR and 13…”

Section: Supporting Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

Gritzapis

Varras

Andreou

et al. 2020

Beilstein J. Org. Chem.

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“…7-Amino-4-methylcoumarin (7-amino-4-methyl-2H-chromen-2-one; NA5) showed the lowest MIC of 1 mg/L against H37Rv strain. Reddy et al [36] synthesized a series of coumarin-oxime ether using the SN 2 reaction of bromomethyl coumarins with butane-2,3-dione monoxime and the derivatives were tested for in vitro anti-TB activity against MTBH 37 Rv strain. The compound (1 h) was found to be the most active by exhibiting MIC of 0.04 μg/ml which is closer to the MIC value of standard drug isoniazid (0.02 μg/ml).…”

Section: Antitubercular Activitymentioning

confidence: 99%

Coumarins: A Unique Scaffold With Versatile Biological Behavior

Gupta¹,

Kumar²,

Chaudhary³

2019

Asian J Pharm Clin Res

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Benzopyrones are the club of compounds that can be coumarins or flavonoids. The hydroxyl derivatives of coumarins such as 4-hydroxycoumarins and 7-hydroxycoumarins have extensive biological activities which have employed for the synthesis of miscellaneous coumarin derivatives. These derivatives have exhibited impressive pharmacological and physiological activities such as anticoagulant, antibacterial, antiviral, antitumor, bactericidal, fungicidal, anti-inflammatory agents, and anti-HIV activity. This review comprised pharmacokinetic studies, including absorption, distribution, and metabolism of coumarin analogs along with toxicological studies. The studies of coumarins and their derivatives exhibiting immense pharmacological activity are also summarized in the current study.

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“…Coumarins containing basic scaffold 1,2‐benzopyrone or 2 H ‐1‐benzopyran‐2‐one is esteemed “privileged” structural motif, which is distributed extensively in a large number of natural products such as plants, essential oils, and microorganisms including few animal species . The unique structure of coumarin and its analog readily interact with a variety of biomacromolecules and stabilizes target binding through various weak interactions . Hence, coumarin‐derived compounds have been explored as promising lead targets in medicinal chemistry possessing broad spectrum of biological activities including anticoagulant, anti‐inflammatory, antitumor, anti‐HIV, antiviral, antioxidant, antimicrobial, antidiabetic, anti‐hyperglycemic, and anticarcinogenic activity .…”

Section: Introductionmentioning

confidence: 99%

Interaction of coumarin triazole analogs to serum albumins: Spectroscopic analysis and molecular docking studies

Sharma

Yadav

Sharma

et al. 2020

J of Molecular Recognition

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The interaction of triazole substituted 4-methyl-7-hydroxycoumarin derivatives (CUM1-4) with serum albumin (bovine serum albumin [BSA] and human serum albumin[HSA]) have been studied employing ultraviolet-visible (UV-Vis), fluorescence, circular dichroism (CD) spectroscopy, and molecular docking methods at physiological pH 7.4.The fluorescence quenching occurred with increasing concentration of CUMs, and the binding constant of CUM derivatives with BSA and HSA obtained from fluorescence quenching experiment was found to be~10 4 L mol −1 . CD study showed conformational changes in the secondary structure of serum albumin upon titration of CUMs.The observed experimental results were further validated by theoretical studies involving density functional theory (DFT) and molecular docking. K E Y W O R D S circular dichroism, coumarin, fluorescence quenching, molecular docking, serum albumin

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Synthesis and evaluation of novel coumarin-oxime ethers as potential anti-tubercular agents: Their DNA cleavage ability and BSA interaction study

Cited by 70 publications

References 56 publications

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

Coumarins: A Unique Scaffold With Versatile Biological Behavior

Interaction of coumarin triazole analogs to serum albumins: Spectroscopic analysis and molecular docking studies

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