Article
Chemistry, Multidisciplinary
Poonam Shaifali, Poonam Sharma, Pushkar Mehara, Pralay Das
Summary: In this study, a heterogeneous and recyclable Pd@PS catalyst was utilized for the synthesis of potentially bioactive 2-(alkylamino/amino)-3-arylquinazolin-4(3H)-one analogues through a tandem addition and intramolecular aminocarbonylative cyclization approach. Various substituted 2-(alkylamino)-3-arylquinazolin-4(3H)-ones were selectively produced in good to excellent yields using amines as nucleophiles and oxalic acid as an ex-situ CO alternative. Furthermore, the gram scale applicability, diverse substrate scope, and high recyclability of the Pd@PS catalyst were significant achievements of this study.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Medicinal
Hariharan Moorthy, Mamta Yadav, Nitesh Tamang, Sai Kiran Mavileti, Labhini Singla, Angshuman Roy Choudhury, Dinkar Sahal, Nageswara Rao Golakoti
Summary: A series of 3,5-diarylidenetetrahydro-2H-pyran-4(3H)-ones (DATPs) were synthesized and evaluated for their antiplasmodial activities against Plasmodium falciparum. Some of the compounds showed high toxicity against the parasite and were non-toxic to mice.
Article
Chemistry, Applied
Shreedhar Devkota, Muhammad Saeed Akhtar, Yong Rok Lee
Summary: This study explores the rhodium(III)-catalyzed sp(2)/sp(3) C-H activation/annulation of 2-arylquinazolin-4(3H)-ones with 3-methylmaleimides. Diversely functionalized isoindoloquinazolinones were obtained in good yields upon reaction with various maleimides. This Rh(III)-catalyzed protocol can be applied for the chemo- and diastereoselective synthesis of various polyheterocycles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Simiaomiao Wen, Yifan Du, Yiwen Liu, Xiaofeng Cui, Qixing Liu, Haifeng Zhou
Summary: A novel approach for synthesizing 2-arylquinazolin-4(3H)-ones was developed using I2/DMSO-mediated intramolecular oxidative cross-coupling, resulting in good functional group tolerance and yields for gram-scale synthesis. The proposed reaction pathway was based on control experiments.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Safinaz E-S. Abbas, Nagwa M. Abdel-Gawad, Riham F. George, Mohamed G. Abu Elyazid, Marwa A. Zaater, Mohamed K. El-Ashrey
Summary: Different 6-iodo-2-(4-bromophenyoxymethyl)-3-substituted quinazolin-4-ones were synthesized and evaluated for their cytotoxic and EGFR inhibitory activities. Compounds 8, 9, 11a, and 11b exhibited superior activity, suggesting their potential as anticancer agents with EGFR inhibitory activity.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Mu-Wang Chen, Minhao Lou, Zhihong Deng, Qin Yang, Yiyuan Peng
Summary: An efficient method for the synthesis of beta-aryl ketones bearing the quinazolin-4(3H)-one scaffold was developed using Rh(III)-catalyzed C-H activation of arenes and C-C cleavage of cyclopropanols. This method has a wide substrate applicability and provides theoretical guidance for future research on quinazoline compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Apurba Dutta, Diganta Sarma
Summary: A metal, solvent and oxidant free method has been developed for the synthesis of quinazolin-4(3H)-ones under microwave irradiation. Using the same catalyst, 2,3-dihydroquinazolin-4(1H)-ones were also synthesized in water as a green and sustainable solvent. These protocols offer a simplistic and rapid approach for assembling diverse structural quinazolinones.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2021)
Article
Chemistry, Multidisciplinary
Cheng-Peng Sun, Xiang-Ge Tian, Lei Feng, Chao Wang, Jing-Xin Li, Xiao-Kui Huo, Wen-Yu Zhao, Jing Ning, Zhen-Long Yu, Sa Deng, Bao-Jing Zhang, Xia Lv, Jie Hou, Xiao-Chi Ma
Summary: The study found that ethanol extracts of black tea showed significant inhibitory activities against Escherichia coli beta-glucuronidase, with some polyphenols being identified as stronger inhibitors. This provides important information for the development of black tea and its constituents for treating drug-induced enteropathy.
ARABIAN JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Tingzhi Lin, Yan-En Wang, Ning Cui, Miaohui Li, Rui Wang, Jiahui Bai, YiRan Fan, Dan Xiong, Fei Xue, Patrick J. Walsh, Jianyou Mao
Summary: A nickel-catalyzed cross-electrophile coupling reaction between 1,2,3-benzotriazin-4(3H)-ones and aryl bromides has been developed, leading to a diverse array of ortho-arylated benzamide derivatives. The reaction exhibits good functional group tolerance and utilizes the ring opening of benzotriazinones followed by denitrogenation to obtain various benzamide derivatives (29 examples, 42-93% yield). The scalability of this transformation has been demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tingzhi Lin, Yan-En Wang, Ning Cui, Miaohui Li, Rui Wang, Jiahui Bai, YiRan Fan, Dan Xiong, Fei Xue, Patrick J. Walsh, Jianyou Mao
Summary: A nickel-catalyzed cross-electrophile coupling reaction has been developed to generate a diverse array of ortho-arylated benzamide derivatives. The reaction shows good functional group tolerance and scalability.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Food Science & Technology
Makoto Kuji, Nanako Itoh, Yui Ohba, Kiyoshi Yamada, Kei Hashimoto
Summary: The study found that 4-ethylcatechol can inhibit the activity of beta-glucuronidase, reducing the risk of colon cancer. 4-ethylcatechol is a competitive inhibitor of beta-glucuronidase, and the ethyl moiety and catechol structure are crucial for its inhibitory activity.
FOOD SCIENCE AND TECHNOLOGY RESEARCH
(2021)
Article
Chemistry, Organic
Bipin Kumar Behera, Sudip Shit, Subhamoy Biswas, Anil K. Saikia
Summary: An efficient methodology for the synthesis of di- and trisubstituted thiazol-2(3H)-ones from N-propargylamines and silver(I) trifluoromethanethiolate has been developed. The reaction proceeds through [3,3]-sigmatropic rearrangement/5-exodig cyclization of N-propargylamines. The starting material can be easily prepared via the A3-coupling reaction of amines, aldehydes, and alkynes. The methodology can also be extended to the synthesis of thiozole-2(3H)thione derivatives, and the photophysical properties of some synthesized compounds have been studied.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Medicinal
Hussein I. El-Subbagh, Mohamed A. Sabry
Summary: Antifolates are a class of drugs used for antibacterial, antiparasitic, and anticancer purposes. 2-substituted-mercapto-quinazolin-4(3H)-one analogues have been studied as DHFR inhibitors, with the development of compounds with significant biological activity based on a structural model. The compounds 18, 20, and 21, formulated using this model, have shown 4-8 times greater activity than the reference drug methotrexate (MTX, 1).
MINI-REVIEWS IN MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wuji Sun, Xue Ma, Yuqi Pang, Lifeng Zhao, Qidi Zhong, Chunyan Liu, Qiangwen Fan
Summary: A green, simple and efficient method for the synthesis of quinazolin-4(3H)-ones has been developed via visible light-induced condensation cyclization. The method utilizes fluorescein as a photocatalyst and TBHP as a reaction promoter without the need for a metal catalyst. The reaction demonstrates high substrate tolerance and yields a variety of desired products in good to excellent yields. This method provides a straightforward strategy for the synthesis of quinazolin-4(3H)-ones.
Article
Biochemistry & Molecular Biology
Tatyana N. Moshkina, Emiliya Nosova, Julia Permyakova, Galina N. Lipunova, Ekaterina F. Zhilina, Grigory A. Kim, Pavel A. Slepukhin, Valery N. Charushin
Summary: This study describes the design and synthesis of compounds with Et2N, Ph2N, or carbazole-9-yl electron donating fragments, and investigates their photophysical properties. The influence of different donor fragments on fluorescence quantum yields and emission intensity is demonstrated. Some compounds show enhanced fluorescence intensity in response to the addition of water in solution.
Article
Chemistry, Applied
Rashadul Hossain, Rajia Sultana, Md Din Islam, Shahed Zaman, Muhammad Iqbal Choudhary
Summary: Two new triterpene glycosides were isolated from the fruits of Terminalia arjuna, along with five known analogues. Their structures were determined through extensive spectroscopic studies. The compounds showed moderate inhibitory activity against α-chymotrypsin.
NATURAL PRODUCT RESEARCH
(2023)
Article
Chemistry, Applied
Raza Ali, Kayode Muritala Salawu, Muhammad Aamer, Humera Jahan, Priya Tufail, Rimsha Irshad, Farooq-Ahmad Khan, Bilge Sener, M. Iqbal Choudhary, Yan Wang
Summary: A new sesquiterpene and several reported compounds were isolated from Prosopis africana, and compound 3 exhibited moderate anti-glycation activity.
NATURAL PRODUCT RESEARCH
(2023)
Article
Chemistry, Applied
Ibrahim Abdurrahman Adam, Rimsha Irshad, Atia-tul-Wahab, Damilola Alex Omoboyowa, M. Iqbal Choudhary, Yan Wang
Summary: Six 5(14)-membered ring type of cyclopeptide alkaloids (CPAs), including two undescribed members, were isolated from the root bark of Ziziphus spina-christi (L.) Desf. Their structures were determined by multiple spectral analyses, and none of them showed cytotoxicity towards tested cell lines.
NATURAL PRODUCT RESEARCH
(2023)
Article
Chemistry, Medicinal
Faiza Saleem, Khalid Mohammed Khan, Nisar Ullah, Musa Ozil, Nimet Baltas, Shehryar Hameed, Uzma Salar, Abdul Wadood, Ashfaq Ur Rehman, Mukesh Kumar, Muhammad Taha, Syed Moazzam Haider
Summary: A library of novel pyridone derivatives was designed, synthesized, and evaluated for their potential as inhibitors of alpha-amylase and alpha-glucosidase, as well as antioxidants. The synthetic compounds showed promising inhibition potential and moderate antioxidant activity. They may serve as lead candidates for controlling diabetes and as antioxidants.
ARCHIV DER PHARMAZIE
(2023)
Article
Chemistry, Multidisciplinary
Amber Ata, Khalid Mohammed Khan, Mehreen Lateef, Uzma Salar, Ayaz Anwar, Abdul Wadood, Ashfaq Ur Rehman, Shehryar Hameed, Fatima Zafar, Muhammad Taha, Shahnaz Perveen
Summary: Several S-substituted-2-mercaptobenzimidazole derivatives were synthesized and evaluated for their urease inhibitory and DPPH radical scavenging activities. The impact of substitutions on the urease inhibitory potential was analyzed, and a structure-activity relationship (SAR) was established. Molecular docking studies revealed the binding interactions of these molecules with the active pocket of urease enzyme.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Muhammad Taha, Mohammed Salahuddin, Noor Barak Almandil, Rai Khalid Farooq, Fazal Rahim, Nizam Uddin, Muhammad Nawaz, Amani H. Alhibshi, El Hassane Anouar, Khalid Mohammed Khan
Summary: In this study, a series of oxadiazole based derivatives were designed and evaluated for their inhibitory potential against alpha-glucosidase. Several analogues showed excellent activity, surpassing the standard drug acarbose. Docking studies confirmed the binding interactions of these active derivatives, and their inhibition of alpha-glucosidase was thermodynamically favored.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Biochemistry & Molecular Biology
Fazal Rahim, Hayat Ullah, Muhammad Taha, Rafaqat Hussain, Maliha Sarfraz, Rashid Iqbal, Naveed Iqbal, Shoaib Khan, Syed Adnan Ali Shah, Marzough Aziz Albalawi, Mahmoud A. Abdelaziz, Fatema Suliman Alatawi, Abdulrahman Alasmari, Mohamed I. Sakran, Nahla Zidan, Ibrahim Jafri, Khalid Mohammed Khan
Summary: Triazole-based thiosemicarbazone derivatives were synthesized and characterized by spectroscopic techniques. Two derivatives, 6i and 6b, showed strong inhibitory effects on acetylcholinesterase and butyrylcholinesterase enzymes. Molecular docking studies revealed their binding interactions with the active sites of the targeted enzymes.
Article
Chemistry, Organic
Muhammad Taha, Mohammed Salahuddin, Fazal Rahim, Syahrul Imran, Shafqat Hussain, Nizam Uddin, Khalid Mohammed Khan
Summary: A series of 7-quinolinyl bearing 1,3,4-thiadiazole-2-amine analogues were synthesized and screened for their inhibitory activity against alpha-amylase and alpha-glucosidase. The analogues showed moderate to good inhibitory potentials, with the most potent inhibitors having fluorine substitution at the phenyl ring of the 1,3,4-thiadiazole ring. The structures of the analogues were confirmed using spectroscopic techniques, and molecular docking studies supported the experimental data. One of the analogues with the strongest inhibitory activity was further screened in a diabetic animal model.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Medicinal
Bushra Adalat, Fazal Rahim, Wajid Rehman, Zarshad Ali, Liaqat Rasheed, Yousaf Khan, Thoraya A. Farghaly, Sulaiman Shams, Muhammad Taha, Abdul Wadood, Syed A. A. Shah, Magda H. Abdellatif
Summary: Twenty-one analogs based on benzimidazole, incorporating a substituted benzaldehyde moiety (1-21), were synthesized and screened for their acetylcholinesterase and butyrylcholinesterase inhibition profiles. Compound 3 showed the most potent activity due to the presence of chloro groups at the 3 and 4 positions of the phenyl ring. Molecular dynamics simulations revealed that compound 3 formed the most stable complex with both acetylcholinestrase and butyrylcholinesterase, displaying higher binding affinities compared to the standard inhibitor donepezil.
Article
Chemistry, Medicinal
Imran Khan, Wajid Rehman, Fazal Rahim, Rafaqat Hussain, Shoaib Khan, Srosh Fazil, Liaqat Rasheed, Muhammad Taha, Syed Adnan Ali Shah, Magda H. Abdellattif, Thoraya A. Farghaly
Summary: This study synthesized benzotriazole-based bis-Schiff base scaffolds (1-20) and evaluated their inhibitory potential on alpha-glucosidase in vitro. All the synthetic analogs exhibited significant inhibition against the enzyme. The IC(50) values of the synthetic scaffolds ranged from 1.10 +/- 0.05 μM to 28.30 +/- 0.60 μM, compared to acarbose as the standard drug (IC50 = 10.30 +/- 0.20 μM). Molecular docking studies supported the experimental data and revealed the binding mode of the active inhibitors with the enzyme's active sites.
Article
Chemistry, Medicinal
Muhammad Taha, Fazal Rahim, Shawkat Hayat, Sridevi Chigurupati, Khalid Mohammed Khand, Syahrul Imran, Syed Adnan Ali Shah, Nizam Uddin, Shatha Ghazi Felemban, Vijayan Venugopal
Summary: Aim: The aim of this study was to synthesize pyrrolopyridine-based thiazolotriazoles as a novel class of alpha-amylase and alpha-glucosidase inhibitors and determine their enzymatic kinetics. Methodology: Pyrrolopyridine-based thiazolotriazole analogs (1-24) were synthesized and characterized through various spectroscopic techniques. Results: The synthesized analogs exhibited significant inhibitory potential against alpha-amylase and alpha-glucosidase, with analog 3 showing the highest inhibitory activity. The structure-activity relationship and binding modes of interactions were confirmed through docking and enzymatic kinetics studies. The compounds (1-24) showed no cytotoxicity against the 3T3 mouse fibroblast cell line.
FUTURE MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Physical
Shawkat Hayat, Hayat Ullah, Fazal Rahim, Ikram Ullah, Muhammad Taha, Naveed Iqbal, Fahad Khan, Muhammad Saleem Khan, Syed Adnan Ali Shah, Abdul Wadood, Muhammad Sajid, Ashraf N. Abdalla
Summary: This study synthesized benzimidazole derivatives for the treatment of diabetes, which exhibited excellent α-glucosidase inhibitory activity compared to clinically used inhibitors.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Muhammad Taha, Aftab Ahmad Khan, Fazal Rahim, Shawkat Hayat, Syahrul Imran, Naveed Iqbal, Nizam Uddin, Khalid Mohammed Khan, El Hassane Anouar, Rai Khalid Farooq, Muhammad Nawaz, Syed Adnan Ali Shah
Summary: In this study, a series of 4-quinolinyl based 1,3,4-thiadiazole-2-amine scaffolds (1-19) were synthesized and evaluated for their in vitro inhibition against alpha-amylase and alpha-glucosidase enzymes. The newly synthesized scaffolds demonstrated varying degrees of inhibitory activity, with compounds 2, 3, and 4 being the most potent inhibitors. The presence of fluorine and chlorine groups at different positions of the phenyl ring attached to the thiadiazole ring may contribute to the enhanced inhibitory profile of these scaffolds. Spectroscopic techniques and molecular docking studies were used to confirm the structures and understand the binding mode of the inhibitors. ADMET prediction and in silico drug likeness analysis showed satisfactory ADMET profile and drug likeness for the synthesized analogues.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Medicinal
Faiza Seraj, Khalid Mohammed Khan, Jamshed Iqbal, Aqeel Imran, Zahid Hussain, Uzma Salar, Shehryar Hameed, Muhammad Taha
Summary: In this study, quinoline-based acyl thiourea derivatives were synthesized and tested for their inhibitory activity against urease. The results showed that 19 derivatives exhibited enhanced inhibitory potential, with compounds possessing specific substituents demonstrating greater inhibition. Molecular docking studies revealed the interaction between these compounds and the active site of the enzyme.
FUTURE MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Mehwish Solangi, Khalid Mohammed Khan, Xingyue Ji, Musa Ozil, Nimet Baltas, Uzma Salar, Alamgir Khan, Zaheer Ul Haq, Herchand Meghwar, Muhammad Taha
Summary: This study synthesized and evaluated a series of indole-pyridine carbonitrile derivatives for their antidiabetic and antioxidant activities. Twelve compounds showed potent inhibitory activities against alpha-glucosidase and alpha-amylase enzymes, making them promising candidates for controlling diabetes.
FUTURE MEDICINAL CHEMISTRY
(2023)
