Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies

Palanichamy Santhosh Kumar; Dhanaraj Premnath; Asir Obadiah; Arulappan Durairaj; Subramanian Ramanathan; Samuel Vasanthkumar

doi:10.1007/s40495-019-00199-0

Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies

Palanichamy Santhosh Kumar
, Dhanaraj Premnath
, Asir Obadiah
, Arulappan Durairaj
, Subramanian Ramanathan
, Samuel Vasanthkumar

Karunya University

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

A series of 3-amino-5-(5-oxo-5H-benzo[a]phenothiazin-6-ylamino) benzoic acid derivatives were synthesized by the Michael addition of 2,3-dichloronaphthalene-1,4-dione and 3,5-diaminobenzoic acid. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa), and antioxidant activity. DPPH and ABTS evaluation procedures are employed to assess the antioxidant activity. Among the synthesized derivatives (1, 2, 3a–g), the compound 3d exhibited the highest inhibition of 77% and 80% in the DPPH and ABTS antioxidant activity evaluation, respectively. The compound 3d exhibited better glide and E model scores when docked with HDAC8 using the GLIDE program. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa), and compound 3d showed the maximum inhibition and displayed a better activity than the standard drug.

Original language	English
Pages (from-to)	440-459
Number of pages	20
Journal	Current Pharmacology Reports
Volume	5
Issue number	6
DOIs	https://doi.org/10.1007/s40495-019-00199-0
State	Published - 1 Dec 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019, Springer Nature Switzerland AG.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

2,3-Dichloronaphthalene-1,4-dione
Antioxidant activity
Cytotoxicity
HeLa cell lines
Michael addition
Molecular docking

Access to Document

10.1007/s40495-019-00199-0

Fingerprint

Dive into the research topics of 'Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies'. Together they form a unique fingerprint.

Cite this

Kumar, P. S., Premnath, D., Obadiah, A., Durairaj, A., Ramanathan, S., & Vasanthkumar, S. (2019). Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies. Current Pharmacology Reports, 5(6), 440-459. https://doi.org/10.1007/s40495-019-00199-0

@article{dd8272fe4428421e92cf899fa3f2cc70,

title = "Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies",

abstract = "A series of 3-amino-5-(5-oxo-5H-benzo[a]phenothiazin-6-ylamino) benzoic acid derivatives were synthesized by the Michael addition of 2,3-dichloronaphthalene-1,4-dione and 3,5-diaminobenzoic acid. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa), and antioxidant activity. DPPH and ABTS evaluation procedures are employed to assess the antioxidant activity. Among the synthesized derivatives (1, 2, 3a{\textendash}g), the compound 3d exhibited the highest inhibition of 77\% and 80\% in the DPPH and ABTS antioxidant activity evaluation, respectively. The compound 3d exhibited better glide and E model scores when docked with HDAC8 using the GLIDE program. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa), and compound 3d showed the maximum inhibition and displayed a better activity than the standard drug.",

keywords = "2,3-Dichloronaphthalene-1,4-dione, Antioxidant activity, Cytotoxicity, HeLa cell lines, Michael addition, Molecular docking",

author = "Kumar, \{Palanichamy Santhosh\} and Dhanaraj Premnath and Asir Obadiah and Arulappan Durairaj and Subramanian Ramanathan and Samuel Vasanthkumar",

note = "Publisher Copyright: {\textcopyright} 2019, Springer Nature Switzerland AG.",

year = "2019",

month = dec,

day = "1",

doi = "10.1007/s40495-019-00199-0",

language = "אנגלית",

volume = "5",

pages = "440--459",

journal = "Current Pharmacology Reports",

issn = "2198-641X",

publisher = "Springer Science and Business Media Deutschland GmbH",

number = "6",

}

Kumar, PS, Premnath, D, Obadiah, A, Durairaj, A, Ramanathan, S & Vasanthkumar, S 2019, 'Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies', Current Pharmacology Reports, vol. 5, no. 6, pp. 440-459. https://doi.org/10.1007/s40495-019-00199-0

Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies. / Kumar, Palanichamy Santhosh; Premnath, Dhanaraj; Obadiah, Asir et al.
In: Current Pharmacology Reports, Vol. 5, No. 6, 01.12.2019, p. 440-459.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies

AU - Kumar, Palanichamy Santhosh

AU - Premnath, Dhanaraj

AU - Obadiah, Asir

AU - Durairaj, Arulappan

AU - Ramanathan, Subramanian

AU - Vasanthkumar, Samuel

PY - 2019/12/1

Y1 - 2019/12/1

N2 - A series of 3-amino-5-(5-oxo-5H-benzo[a]phenothiazin-6-ylamino) benzoic acid derivatives were synthesized by the Michael addition of 2,3-dichloronaphthalene-1,4-dione and 3,5-diaminobenzoic acid. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa), and antioxidant activity. DPPH and ABTS evaluation procedures are employed to assess the antioxidant activity. Among the synthesized derivatives (1, 2, 3a–g), the compound 3d exhibited the highest inhibition of 77% and 80% in the DPPH and ABTS antioxidant activity evaluation, respectively. The compound 3d exhibited better glide and E model scores when docked with HDAC8 using the GLIDE program. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa), and compound 3d showed the maximum inhibition and displayed a better activity than the standard drug.

AB - A series of 3-amino-5-(5-oxo-5H-benzo[a]phenothiazin-6-ylamino) benzoic acid derivatives were synthesized by the Michael addition of 2,3-dichloronaphthalene-1,4-dione and 3,5-diaminobenzoic acid. All the synthesized compounds are screened for their bioactivity through molecular docking, cytotoxicity (against HeLa), and antioxidant activity. DPPH and ABTS evaluation procedures are employed to assess the antioxidant activity. Among the synthesized derivatives (1, 2, 3a–g), the compound 3d exhibited the highest inhibition of 77% and 80% in the DPPH and ABTS antioxidant activity evaluation, respectively. The compound 3d exhibited better glide and E model scores when docked with HDAC8 using the GLIDE program. Cytotoxicity of the synthesized compounds was studied against cervical cancer cell line (HeLa), and compound 3d showed the maximum inhibition and displayed a better activity than the standard drug.

KW - 2,3-Dichloronaphthalene-1,4-dione

KW - Antioxidant activity

KW - Cytotoxicity

KW - HeLa cell lines

KW - Michael addition

KW - Molecular docking

UR - https://www.scopus.com/pages/publications/85076615540

U2 - 10.1007/s40495-019-00199-0

DO - 10.1007/s40495-019-00199-0

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:85076615540

SN - 2198-641X

VL - 5

SP - 440

EP - 459

JO - Current Pharmacology Reports

JF - Current Pharmacology Reports

IS - 6

ER -

Synthesis, Structure Characterization, and Biological Evaluation of 3-Amino-5-(5-Oxo-5H-Benzo[a]Phenothiazin-6-Ylamino) Benzoic Acid Derivatives via Molecular Docking, Cytotoxicity, and Antioxidant Studies

Abstract

Bibliographical note

UN SDGs

Keywords

Access to Document

Other files and links

Fingerprint

Cite this