scholarly journals Ethyl (S)-2-Benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate

Molbank ◽  
10.3390/m1166 ◽  
2020 ◽  
Vol 2020 (4) ◽  
pp. M1166
Author(s):  
Mario Leyva-Acuña ◽  
Francisco Delgado-Vargas ◽  
Gabriela López-Angulo ◽  
Julio Montes-Avila
Keyword(s):  
Microwave Irradiation ◽  
Ethyl Ester ◽  
13C Nmr ◽  
Biological Activities ◽  
The Novel ◽  
Ester Hydrochloride ◽  
Pyrimidine Derivatives ◽  
Wide Range ◽  
Atr Spectroscopy ◽  
Moderate Yield

Pyrimidines are compounds with a wide range of biological activities, and the synthesis of pyrimidine derivatives—useful in chemical and medicinal applications—is important in medicinal chemistry. This work shows the synthesis under microwave irradiation of the novel compound ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate (3) from (S)-N-α-benzoyl-l-arginine ethyl ester hydrochloride (1) and acetylacetone (2). Compound 3 was easily purified, obtained in moderate yield (70%), and fully characterized by UV-Vis, FTIR-ATR spectroscopy, 1H-NMR, 13C-NMR, HRMS, and EI-MS.

scholarly journals Synthesis of Novel 2-(Pyridin-2-yl) Pyrimidine Derivatives and Study of Their Anti-Fibrosis Activity

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5226
Author(s):  
Yi-Fei Gu ◽  
Yue Zhang ◽  
Feng-li Yue ◽  
Shao-tong Li ◽  
Zhuo-qi Zhang ◽  
...  
Keyword(s):  
Biological Activities ◽  
Collagen Type I ◽  
Type I ◽  
The Novel ◽  
Pyrimidine Derivatives ◽  
Wide Range ◽  
Ic50 Values ◽  
Privileged Structures ◽  
Pyrimidine Moiety

A pyrimidine moiety exhibiting a wide range of pharmacological activities has been employed in the design of privileged structures in medicinal chemistry. To prepare libraries of novel heterocyclic compounds with potential biological activities, a series of novel 2-(pyridin-2-yl) pyrimidine derivatives were designed, synthesized and their biological activities were evaluated against immortalized rat hepatic stellate cells (HSC-T6). Fourteen compounds were found to present better anti-fibrotic activities than Pirfenidone and Bipy55′DC. Among them, compounds ethyl 6-(5-(p-tolylcarbamoyl)pyrimidin-2-yl)nicotinate (12m) and ethyl 6-(5-((3,4-difluorophenyl)carbamoyl)pyrimidin-2-yl)nicotinate (12q) show the best activities with IC50 values of 45.69 μM and 45.81 μM, respectively. Furthermore, the study of anti-fibrosis activity was evaluated by Picro-Sirius red staining, hydroxyproline assay and ELISA detection of Collagen type I alpha 1 (COL1A1) protein expression. Our study showed that compounds 12m and 12q effectively inhibited the expression of collagen, and the content of hydroxyproline in cell culture medium in vitro, indicating that compounds 12m and 12q might be developed the novel anti-fibrotic drugs.

Design, Synthesis and Biological Evaluation of the Novel Antitumor Agent Aurone Derivatives

2013 ◽  
Vol 781-784 ◽  
pp. 1235-1239
Author(s):  
Qian Nan Guo ◽  
Lei Lv ◽  
Yao Zhou ◽  
Peng Yu ◽  
Yuou Teng
Keyword(s):  
Biological Activities ◽  
Antitumor Agent ◽  
Biological Evaluation ◽  
The Novel ◽  
Pharmacological Activities ◽  
Design Synthesis ◽  
H Nmr ◽  
Wide Range ◽  
Inhibitory Activities ◽  
Synthesis And Biological Evaluation

Aurones belong to a class of heterocyclic flavonoids which contains a benzofuran element associated with a benzylidene linked in position 2. Aurones possess a wide range of pharmacological activities and biological activities, such as antitumor, antifungal, phytoalexin and so on. A novel series of 2-ayl-yl (5-methacrylate) aurone analogues were synthesized in six steps with the overall yield of 11%-13% and characterized by 1H NMR. Among the key intermediates and target compounds, 2-(2-furan-ylmethylene)-5-methacrylate-benzofuran-3(2H)-one (7a) and 2-(2-thienyl-ylmethylene)-5-methacrylate-benzofuran-3(2H)-one (7b) have never been reported before. Primary biological activities evaluation showed that 7a exhibited good inhibitory activities against K562 with an IC50 of 2.18 μM and against HepG2 with an IC50 of 3.95μM.

scholarly journals 2-Arylidene-1-indandiones as Pleiotropic Agents with Antioxidant and Inhibitory Enzymes Activities

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4411 ◽  
Author(s):  
Olympia Kouzi ◽  
Eleni Pontiki ◽  
Dimitra Hadjipavlou-Litina
Keyword(s):  
Antioxidant Activities ◽  
Biological Activities ◽  
Knoevenagel Reaction ◽  
The Novel ◽  
Hydrophobic Domain ◽  
Antioxidant Agents ◽  
Wide Range ◽  
Anti Inflammatory

Indandiones are a relatively new group of compounds presenting a wide range of biological activities. The synthesis of these compounds was performed via a Knoevenagel reaction between an aldehyde and 1,3-indandione and were obtained with a yield up to 54%. IR, 1H-Nucleic Magnetic Resonance (NMR), 13C-NMR, LC/MS ESI+ and elemental analysis were used for the confirmation of the structures of the novel derivatives. Lipophilicity values of compounds were calculated theoretically and experimentally by reversed chromatography method as values RM. The novel derivatives were studied through in vitro and in vivo experiments for their activity as anti-inflammatory and antioxidant agents and as inhibitors of lipoxygenase, trypsin, and thrombin. The inhibition of the carrageenin-induced paw edema (CPE) was also determined for representative structures. In the above series of experiments, we find that all the compounds showed moderate to satisfying interaction with the stable DPPH free radical in relation to the concentration and the time 2-arylidene-1-indandione (10) was the strongest. We observed moderate or very low antioxidant activities for selected compounds in the decolorization assay with ABTS+•. Most of the compounds showed high anti-lipid peroxidation of linoleic acid induced by AAPH.2-arylidene-1-indandione (7) showed a strongly inhibited soybean LOX. Only 2-arylidene-1-indandione (3) showed moderate scavenging activity of superoxide anion, whereas 2-arylidene-1-indandione (8) and 2-arylidene-1-indandione (9) showed very strong inhibition on proteolysis. 2-arylidene-1-indandione (8) highly inhibited serine protease thrombin. 2-arylidene-1-indandiones (7, 8 and 9) can be used as lead multifunctional molecules. The compounds were active for the inhibition of the CPE (30–57%) with 2-arylidene-1-indandione (1) being the most potent (57%). According to the predicted results a great number of the derivatives can cross the Blood–Brain Barrier (BBB), act in CNS and easily transported, diffused, and absorbed. Efforts are conducted a) to correlate quantitatively the in vitro/in vivo results with the most important physicochemical properties of the structural components of the molecules and b) to clarify the correlation of actions among them to propose a possible mechanism of action. Hydration energy as EHYDR and highest occupied molecular orbital (HOMO) better describe their antioxidant profile whereas the lipophilicity as RM values governs the in vivo anti-inflammatory activity. Docking studies are performed and showed that soybean LOX oxidation was prevented by blocking into the hydrophobic domain the substrates to the active site.

scholarly journals 5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3173
Author(s):  
Evangelos Mavridis ◽  
Eleftherios Bermperoglou ◽  
Eleni Pontiki ◽  
Dimitra Hadjipavlou-Litina
Keyword(s):  
Lipid Peroxidation ◽  
Biological Activities ◽  
Phenyl Group ◽  
Docking Studies ◽  
Nucleophilic Attack ◽  
The Novel ◽  
Lipoxygenase Inhibitor ◽  
Wide Range ◽  
Inhibit Lipid Peroxidation

The five membered heterocyclic oxazole group plays an important role in drug discovery. Oxazolones present a wide range of biological activities. In this article the synthesis of 4-substituted-2-phenyloxazol-5(4H)-ones from the appropriate substituted aldehydes via an Erlenmeyer–Plochl reaction is reported. Subsequently, the corresponding benzamides were produced via a nucleophilic attack of a secondary amine on the oxazolone ring applying microwave irradiation. The compounds are obtained in good yields up to 94% and their structures were confirmed using IR, 1H-NMR, 13C-NMR and LC/MS data. The in vitro anti-lipid peroxidation activity and inhibitory activity against lipoxygenase and trypsin induced proteolysis of the novel derivatives were studied. Inhibition of carrageenin-induced paw edema (CPE) and nociception was also determined for compounds 4a and 4c. Oxazolones 2a and 2c strongly inhibit lipid peroxidation, followed by oxazolones 2b and 2d with an average inhibition of 86.5%. The most potent lipoxygenase inhibitor was the bisbenzamide derivative 4c, with IC50 41 μM. The benzamides 3c, 4a–4e and 5c were strong inhibitors of proteolysis. The replacement of the thienyl moiety by a phenyl group does not favor the protection. Compound 4c inhibited nociception higher than 4a. The replacement of thienyl groups by phenyl ring led to reduced biological activity. Docking studies of the most potent LOX inhibitor highlight interactions through allosteric mechanism. All the potent derivatives present good oral bioavailability.

scholarly journals (Z)-5-(3′,4′-Bis(benzyloxy)benzylidene)furan-2(5H)-one

Molbank ◽  
10.3390/m1193 ◽  
2021 ◽  
Vol 2021 (1) ◽  
pp. M1193
Author(s):  
Angelica Artasensi ◽  
Giovanna Baron ◽  
Giulio Vistoli ◽  
Giancarlo Aldini ◽  
Laura Fumagalli
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Good Yield ◽  
Biological Activities ◽  
The Novel ◽  
One Pot ◽  
Natural Form ◽  
Bioactive Natural Products ◽  
Beneficial Effects ◽  
Wide Range

Over the years secondary metabolites have been considered as lead molecules both in their natural form and as templates for medicinal chemistry. Some secondary metabolites such as polyphenols and flavan-3-ols exert beneficial effects after a modification by the microbiota. Synthetic precursors of some of these modified compounds, in turn, carried a γ-alkylidenebutenolide moiety which characterizes a large class of bioactive natural products endowed with a wide range of biological activities. For these reasons stereoselective preparation of γ-alkylidenebutenolide continues to be an important issue for organic chemists. Our objective is to synthetize the novel compound (Z)-5-(3′,4′-bis(benzyloxy)benzylidene)furan-2(5H)-one in a stereocontrolled-one-pot reaction. The product was obtained in good yield. Furthermore, the theoretical investigation of the transition states suggests a new procedure to achieve Z-isomer of β-unsubstituted γ-alkylidenebutenolide.

Nanoformulations of Coumarins and the Hybrid Molecules of Coumarins with Potential Anticancer Effects

2020 ◽  
Vol 20 (15) ◽  
pp. 1797-1816 ◽  
Author(s):  
Mukerrem Betul Yerer ◽  
Serkan Dayan ◽  
M. Ihsan Han ◽  
Ajay Sharma ◽  
Hardeep S. Tuli ◽  
...  
Keyword(s):  
Higher Plants ◽  
Biological Activities ◽  
Pharmaceutical Formulations ◽  
The Novel ◽  
Pyrone Ring ◽  
Anticancer Effects ◽  
Hybrid Molecules ◽  
Wide Range ◽  
Leaf Oil ◽  
Relationship Of

Coumarins are the secondary metabolites of some plants, fungi, and bacteria. Coumarins and the hybrid molecules of coumarins are the compounds which have been widely studied for their potential anticancer effects. They belong to benzopyrone chemical class, more precisely benzo-α-pyrones, where benzene ring is fused to pyrone ring. In nature, coumarins are found in higher plants like Rutaceae and Umbelliferae and some essential oils like cinnamon bark oil, cassia leaf oil and lavender oil are also rich in coumarins. The six main classes of coumarins are furanocoumarins, dihydrofuranocoumarins, pyrano coumarins, pyrone substituted coumarins, phenylcoumarins and bicoumarins. As well as their wide range of biological activities, coumarins and the hybrid molecules of coumarins are proven to have an important role in anticancer drug development due to the fact that many of its derivatives have shown an anticancer activity on various cell lines. Osthol, imperatorin, esculetin, scopoletin, umbelliprenin, angelicine, bergamottin, limettin, metoxhalen, aurapten and isopimpinellin are some of these coumarins. This review summarizes the anticancer effects of coumarins and their hybrid molecules including the novel pharmaceutical formulations adding further information on the topic for the last ten years and basically focusing on the structureactivity relationship of these compounds in cancer.

An overview of the synthetic route to the marketed formulations of pyrimidine: A Review

2021 ◽  
Vol 21 ◽  
Author(s):  
Amit Kumar ◽  
Ankit Siwach ◽  
Prabhakar Verma
Keyword(s):  
Heterocyclic Compounds ◽  
Biological Activities ◽  
New Work ◽  
Important Class ◽  
Synthetic Route ◽  
Antiprotozoal Activity ◽  
Pyrimidine Derivatives ◽  
Organic Reaction ◽  
Wide Range ◽  
Pyrimidine Moiety

: Pyrimidine and its derivatives are a very important class of heterocyclic compounds that show interesting applications in the field of medicinal chemistry. Pyrimidine not only plays an important role as an organic reaction intermediate but also has a wide range of interesting biological activities viz. antibacterial, antifungal, anticancer, anti-inflammatory, antiviral, and antiprotozoal activity, etc. Numerous methods are available for the formation of pyrimidine derivatives have been reported in the literature. The advantage of pyrimidine as a starting material for different therapeutically potent derivatives has given momentum to this research. This review aims to report the new work on the synthesis of marketed drugs which consist of pyrimidine moiety.

Mangrove Plants as a Source of Bioactive Compounds: A Review

2019 ◽  
Vol 9 (2) ◽  
pp. 86-97 ◽  
Author(s):  
Nilesh Lakshman Dahibhate ◽  
Ankush Ashok Saddhe ◽  
Kundan Kumar
Keyword(s):  
Natural Products ◽  
Bioactive Compounds ◽  
Raw Materials ◽  
Biological Activities ◽  
Enzyme Activation ◽  
The Novel ◽  
Coastal Forest ◽  
Low Oxygen ◽  
Wide Range ◽  
Harsh Conditions

Mangroves are unique coastal forest ecosystem distributed along the tropical and subtropical region of the world. They are evolutionarily adapted to combat against hostile environmental conditions such as low oxygen, high salinity, and temperature. The adaptive features endowed with novel secondary metabolic pathways and bioactive compounds to sustain in harsh conditions. The novel metabolites are a rich source of the wide range of bioactive compounds and natural products. It includes terpenoids, alkaloids, phenolics, saponins, flavonoids, and steroids. The bioactive and natural compounds may serve as therapeutic precursors and industrial raw materials. Terpenes and polyphenols have antiviral, antibacterial, antifungal, antimalarial, anticancer or combination of activities. To date, several mangroves plants were examined and recognized as a potential source of novel natural product for exploitation in medicine. In fact, most of the isolated compounds are novel and showed promising biological activities such as gastroprotective, cytotoxic, antioxidant, antibacterial, antifungal, antiviral, enzyme activation and inhibition, immunosuppressive, anti-inflammatory, antifeedant effects. In the present review, we have compiled the achievements and progress in mangroves natural products research of the last decade.

Pharmacologically potentials of different substituted coumarin derivatives

2019 ◽  
Author(s):  
Chem Int
Keyword(s):  
Benzene Ring ◽  
Bioactive Compounds ◽  
Biological Activities ◽  
Pharmacological Properties ◽  
Coumarin Derivatives ◽  
Wide Range ◽  
Anti Oxidant ◽  
Anti Inflammatory ◽  
Coumarin Compounds

Coumarin and its derivatives are widely spread in nature. Coumarin goes to agroup as benzopyrones, which consists of a benzene ring connected to a pyronemoiety. Coumarins displayed a broad range of pharmacologically useful profile.Coumarins are considered as a promising group of bioactive compounds thatexhibited a wide range of biological activities like anti-microbial, anti-viral,antiparasitic, anti-helmintic, analgesic, anti-inflammatory, anti-diabetic, anticancer,anti-oxidant, anti-proliferative, anti-convulsant, and antihypertensiveactivities etc. The coumarin compounds have immense interest due to theirdiverse pharmacological properties. In particular, these biological activities makecoumarin compounds more attractive and testing as novel therapeuticcompounds.

Synthesis, Characterization and Antiproliferative Activity Assessment of a Novel 1H-5-mercapto-1,2,4 Triazole Derivative

2017 ◽  
Vol 68 (4) ◽  
pp. 745-747 ◽  
Author(s):  
Marius Mioc ◽  
Sorin Avram ◽  
Vasile Bercean ◽  
Mihaela Balan Porcarasu ◽  
Codruta Soica ◽  
...  
Keyword(s):  
Antiproliferative Activity ◽  
Biological Activities ◽  
Cancer Cell Line ◽  
Vascular Endothelial ◽  
Triazole Derivative ◽  
Activity Assessment ◽  
Wide Range ◽  
Specific Receptors ◽  
Endothelial Growth Factor ◽  
Selection Of

Angiogenesis plays an important function in tumor proliferation, one of the main angiogenic promoters being the vascular endothelial growth factor (VEGF) which activates specific receptors, particularly VEGFR-2. Thus, VEGFR-2 has become an essential therapeutic target in the development of new antitumor drugs. 1,2,4-triazoles show a wide range of biological activities, including antitumor effect, which was documented by numerous reports. In the current study the selection of 5-mercapto-1,2,4-triazole structure (1H-3-styryl-5-benzylidenehydrazino-carbonyl-methylsulfanil-1,2,4-triazole, Tz3a.7) was conducted based on molecular docking that emphasized it as suitable ligand for VEGFR-2 and EGFR1 receptors. Compound Tz3a.7 was synthesized and physicochemically and biologically evaluated thus revealing a moderate antiproliferative activity against breast cancer cell line MDA-MB-231.

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