Synthesis, Biological Evaluation, and Molecular Docking of Novel Azolylhydrazonothiazoles as Potential Anticancer Agents

被引：25

作者：

Al-Humaidi, Jehan Y. ^{[1
]}

Gomha, Sobhi M. ^{[2
]}

Riyadh, Sayed M. ^{[3
]}

Ibrahim, Mohamed S. ^{[2
]}

Zaki, Magdi E. A. ^{[4
]}

Abolibda, Tariq Z. ^{[2
]}

Jefri, Ohoud A. ^{[5
]}

Abouzied, Amr S. ^{[6
,7
]}

机构：

[1] Princess Nourah bint Abdulrahman Univ, Coll Sci, Dept Biol, POB 84428, Riyadh 11671, Saudi Arabia

[2] Islamic Univ Madinah, Fac Sci, Dept Chem, Madinah 42351, Saudi Arabia

[3] Cairo Univ, Fac Sci, Dept Chem, Cairo 12613, Egypt

[4] Imam Mohammad Ibn Saud Islamic Univ IMSIU, Coll Sci, Dept Chem, Riyadh 11623, Saudi Arabia

[5] King Abdulaziz Univ, Fac Sci, Dept Biol Sci, Jeddah 21589, Saudi Arabia

[6] Univ Hail, Coll Pharm, Dept Pharmaceut Chem, Hail 81442, Saudi Arabia

[7] Natl Org Drug Control & Res NODCAR, Dept Pharmaceut Chem, Giza, Egypt

来源：

ACS OMEGA | 2023年 / 8卷 / 37期

关键词：

DERIVATIVES DESIGN; GREEN SYNTHESIS; IN-VITRO; THIAZOLE; EGFR; INHIBITORS; ANTIBACTERIAL; MECHANISM; INDOLES; ANALOGS;

D O I：

10.1021/acsomega.3c05038

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel set of thiazolylhydrazonothiazoles bearing an indole moiety were synthesized by subjection reactions of carbothioamide derivative and hydrazonoyl chlorides (or a-haloketones). The cytotoxicity of the synthesized compounds was evaluated against the colon carcinoma cell line (HCT-116), liver carcinoma cell line (HepG2), and breast carcinoma cell line (MDA-MB-231), and demonstrated encouraging activity. Furthermore, when representative products were assessed for toxicity against normal cells, minimal toxic effects were observed, indicating their potential safety for use in pharmacological studies. The mechanism of action of the tested products, as inhibitors of the epidermal growth factor receptor tyrosine kinase domain (EGFR TK) protein, was suggested through docking studies that assessed their binding scores and modes, in comparison to a reference standard (W19), thus endorsing their anticancer activity.

引用

页码：34044 / 34058

页数：15

共 57 条

[1] Synthesis and Antiviral Activity of New Indole-Based Heterocycles [J].

Abdel-Gawad, Hassan ;

Mohamed, Hanan Ahmed ;

Dawood, Kamal Mohamed ;

Badria, Farid Abdel-Rahem .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (11) :1529-1531

[2] Synthesis of Certain New Thiazole and 1,3,4-Thiadiazole Derivatives via the Utility of 3-Acetylindole [J].

Abdelhamid, Abdou O. ;

Gomha, Sobhi M. ;

Kandeel, Saher M. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) :1529-1536

[3] Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents [J].

Abdelhamid, Abdou O. ;

Gomha, Sobhi M. ;

Abdelriheem, Nadia A. ;

Kandeel, Saher M. .

MOLECULES, 2016, 21 (07)

[4] Design, synthesis and pharmacophoric model building of new 3-alkoxymethyl/3-phenyl indole-2-carboxamides with potential antiproliferative activity [J].

Abdelrahman, Mostafa H. ;

Aboraia, Ahmed S. ;

Youssif, Bahaa G. M. ;

Elsadek, Bakheet E. M. .

CHEMICAL BIOLOGY & DRUG DESIGN, 2017, 90 (01) :64-82

[5] Synthesis, Molecular Docking Study, and Cytotoxicity Evaluation of Some Novel 1,3,4-Thiadiazole as Well as 1,3-Thiazole Derivatives Bearing a Pyridine Moiety [J].

Abouzied, Amr S. ;

Al-Humaidi, Jehan Y. ;

Bazaid, Abdulrahman S. ;

Qanash, Husam ;

Binsaleh, Naif K. ;

Alamri, Abdulwahab ;

Ibrahim, Sheikh Muhammad ;

Gomha, Sobhi M. .

MOLECULES, 2022, 27 (19)

[6] In Silico Pharmacokinetic Profiling of the Identified Bioactive Metabolites of Pergularia tomentosa L. Latex Extract and In Vitro Cytotoxic Activity via the Induction of Caspase-Dependent Apoptosis with S-Phase Arrest [J].

Abouzied, Amr S. ;

Abd-Rabo, Marwa M. ;

Huwaimel, Bader ;

Almahmoud, Suliman A. ;

Almarshdi, Afnan Abdulkareem ;

Alharbi, Fai Mutaz ;

Alenzi, Sulafa Salem ;

Albsher, Bayan Naef ;

Alafnan, Ahmed .

PHARMACEUTICALS, 2022, 15 (09)

[7] Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro) [J].

Abu-Melha, Sraa ;

Edrees, Mastoura M. ;

Riyadh, Sayed M. ;

Abdelaziz, Mohamad R. ;

Elfiky, Abdo A. ;

Gomha, Sobhi M. .

MOLECULES, 2020, 25 (19)

[8] Design and synthesis of new 2,5-disubstituted-1,3,4-oxadiazole analogues as anticancer agents [J].

Agarwal, Mohit ;

Singh, Vikram ;

Sharma, Sachin Kumar ;

Sharma, Piush ;

Ansari, Md. Yousuf ;

Jadav, Surender Singh ;

Yasmin, Sabina ;

Sreenivasulu, Reddymasu ;

Hassan, Mohd. Zaheen ;

Saini, Vipin ;

Ahsan, Mohamed Jawed .

MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (10) :2289-2303

[9] Anticancer Properties of Indole Compounds: Mechanism of Apoptosis Induction and Role in Chemotherapy [J].

Ahmad, Aamir ;

Sakr, Wael A. ;

Rahman, K. M. Wahidur .

CURRENT DRUG TARGETS, 2010, 11 (06) :652-666

[10] Construction, molecular docking, antimicrobial and antioxidant activity of some novel 3-substitued indole derivatives using 3-Acetyl indole [J].

Al-Khaldi, Alanoud ;

Ghoneim, Amira Atef ;

El-sherif, Mervat Ahmed ;

Elbargisy, Rehab ;

Ghanem, Heba Bassiony ;

Zafar, Rehman .

JOURNAL OF SAUDI CHEMICAL SOCIETY, 2021, 25 (11)

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