Structure and absolute configuration of some 5-chloro-2-methoxy-N-phenylbenzamide derivatives

Galal, Alaaeldin M. F.; Shalaby, ElSayed M.; Abouelsayed, A.; Ibrahim, Medhat; Al-Ashkar, Emad A.; Hanna, Atef G.

doi:10.1016/j.saa.2017.06.068

Cited by 15 publications

(10 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5-Chloro-2-methoxy-N-benzyl benzamide (2) was obtained with a 97% yield by the mixed anhydride method. [48] Subsequently, 4-(5-chloro-2-methoxybenzamido-Nmethylene)benzenesulfonyl chloride (3) was obtained with a 90% yield by chlorosulfonation of amide 2. [35] The final sulfonyl-L-amino acid derivatives were synthesized by the application of a simple, efficient, and eco-friendly method under green conditions.…”

Section: Chemistrymentioning

confidence: 99%

Development, synthesis, and biological evaluation of sulfonyl‐α‐l‐amino acids as potential anti‐Helicobacter pylori and IMPDH inhibitors

Galal

Mohamed

Abdel‐Aziz

et al. 2021

Archiv der Pharmazie

View full text Add to dashboard Cite

Inosine 5ʹ-monophosphate dehydrogenase (IMPDH) catalyzes a crucial step in the biosynthesis of DNA and RNA, and it has been exploited as a promising target for antimicrobial therapy. The present study discusses the development and synthesis of a series of sulfonyl-α-L-amino acids coupled with the anisamide scaffold and evaluates their activities as anti-Helicobacter pylori and IMPDH inhibitors. Twenty derivatives were synthesized and their structures were established by highresolution mass spectrometry and 1 H and 13 C nuclear magnetic resonance measurements. Four compounds (6, 10, 11, and 21) were found to be the most potent and selective molecules in the series with minimum inhibitory concentration (MIC) values <17 µM, which were selected to test their inhibitory activities against HpIMPDH and human (h)IMPDH2 enzymes. In all tests, amoxicillin and clarithromycin were used as reference drugs. Compounds 6 and 10 were found to have a promising activity against the HpIMPDH enzyme, with IC 50 = 2.42 and 2.56 µM, respectively. Moreover, the four compounds were found to be less active and safer against hIMPDH2 than the reference drugs, with IC 50 > 17.17 µM, which makes sure that their selectivity is toward HpIMPDH and reverse to that of amoxicillin and clarithromycin. Also, the synergistic antibacterial activity of compounds 6, 10, amoxicillin, and clarithromycin was investigated in vitro. The combination of amoxicillin/compound 6 (2:1 by weight) exhibited a significant antibacterial activity against H. pylori, with MIC = 0.12 µg/ml. The molecular docking study and ADMET analysis of the most active compounds were used to elucidate the mode-of-action mechanism.

show abstract

Section: Chemistrymentioning

confidence: 99%

Development, synthesis, and biological evaluation of sulfonyl‐α‐l‐amino acids as potential anti‐Helicobacter pylori and IMPDH inhibitors

Galal

Mohamed

Abdel‐Aziz

et al. 2021

Archiv der Pharmazie

View full text Add to dashboard Cite

show abstract

“…On the other hand computational methods are utilized extensively to study the electronic; physical and chemical properties of many systems and molecules [8][9][10]. It could be also utilized to study the biomolecules with promising results supporting the experimental findings [11][12][13]. Different level of theories was early utilized to elucidate different properties of glucose as well as other carbohydrates.…”

Section: Introductionmentioning

confidence: 99%

Effect of hydration on the physical properties of glucose

2019

Biointerface Res Appl Chem

View full text Add to dashboard Cite

The effect of hydration on the electronic properties of glucose (Gl) is studied by quantum mechanics by using DFT procedures atB3LYP/6-31g(d,p). Total dipole moment, the highest and the lowest occupied molecular orbital (HOMO/LUMO band gap energy) and molecular electrostatic potentials (ESPs) are calculated at the same level of theory for all model molecules. The results indicated that there is an enhancement in the electronic properties of Gl where TDM of Gl is increased from2.5454Debye to 4.3157Debye while HOMO/LUMO band gap energy is decreased from 13.0994 eV to 3.2749 eV. Also, the calculated ESP results are indicated that the electro-negativity is increased due to hydration which means that the reactivity is increased and hence the electronic properties are improved.

show abstract

“…Accordingly, understanding the structural and electronic properties of CMC is an impotent step toward further application of such important derivative. It is stated that, molecular modeling show potential to study natural polymers as well as many other emerging materials [16][17][18][19]. In this sense molecular modeling at B3LYP/3-21G* level is conducted to study the influence of moisture on the electronic properties of monomer, dimer, trimer and emeraldine base sodium carboxymethyl cellulose.…”

Section: Introductionmentioning

confidence: 99%

The Influence of Moisture on the Electronic Properties of Monomer, Dimer, Trimer and Emeraldine Base Sodium Carboxymethyl Cellulose

et al. 2019

View full text Add to dashboard Cite

A CCORDING to previous studies on moisture effect, it is stated that moisture enhances the electronic properties of polymeric materials. A theoretical study based on density functional theory calculations at B3LYP/3-21G* is performed for investigating the effect of moisture on sodium carboxymethyl cellulose (Na-CMC) as monomer, dimer, trimer and emeraldine base. Results indicated that due to moisture, TDM is increased while HOMO/ LUMO band gap energy is decreased for the four proposed structures for Na-CMC. All results indicated that there is a change occurring in the electronic properties as a result of moisture. Furthermore, as a result of increasing the degree of polymerization, the total dipole moment (TDM) of Na-CMC is increased and equals 7.7141, 28.0388, 24.0199 and 38.3464 Debye for monomer Na-CMC, dimer Na-CMC, trimer Na-CMC and emeraldine base Na-CMC respectively. However, the highest occupied and the lowest unoccupied energy gap (HOMO/ LUMO band gap energy) decreased and equals 0.9040, 0.3448, 0.1241 and 0.9021 eV for the same sequence. Additionally, the results of ESP study of all model molecules are in good agreement with the results of TDM and HOMO/LUMO band gap energy. Keywords: B3LYP/3-21G*; Na-CMC; TDM; HOMO/LUMO band gap energy and ESP.

show abstract

Structure and absolute configuration of some 5-chloro-2-methoxy-N-phenylbenzamide derivatives

Cited by 15 publications

References 25 publications

Development, synthesis, and biological evaluation of sulfonyl‐α‐l‐amino acids as potential anti‐Helicobacter pylori and IMPDH inhibitors

Development, synthesis, and biological evaluation of sulfonyl‐α‐l‐amino acids as potential anti‐Helicobacter pylori and IMPDH inhibitors

Effect of hydration on the physical properties of glucose

The Influence of Moisture on the Electronic Properties of Monomer, Dimer, Trimer and Emeraldine Base Sodium Carboxymethyl Cellulose

Contact Info

Product

Resources

About