Aqueous extract of Balanites roxburghii fruit: a green dispersant for C–C bond formation

Barge, Madhuri; Salunkhe, Rajashri

doi:10.1039/c4ra04387a

Cited by 22 publications

(11 citation statements)

References 54 publications

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“…It is known that Knoevenagel condensation reactions yields are influenced by the stereochemistry of the used aldehyde. Compounds 1, 3, 4, 5, 6, 10 have been synthesized earlier under different experimental conditions [38,39,40,41,42,43,44,45,46,47,48,49,50,51]. We used a different synthetic technique and the structures of the known compounds were verified according to the given in the literature spectral data, elemental analysis, or mps.…”

Section: Resultsmentioning

confidence: 99%

“…176–177 °C; IR (Nujol) (cm −1 ): 1720, 1680, 1600, 730; 1 H-NMR (300 MHz, CDCl 3 ): δ (ppm) 7.78–7.81 (m, 2H, aromatics), 7.88 (d, 1H, aromatic, J = 5.5 Hz), 7.97–8.03 (m, 5H, aromatic and C=C H ); 13 C-NMR (75 MHz, CDCl 3 ): 123.0, 123.1, 128.6, 134.9, 135.2, 136.3, 138.2, 141.7, 150.6, 173.6, 186.2, 187.3, 200.5, 203.5; Anal. C, H. Calcd %: (C14H8O2S) C: 69.98, H: 3.36 Found %: C: 70.4, H: 3.31 [38,39,40,41].…”

Section: Methodsmentioning

confidence: 99%

“…Some of these derivatives, compounds 1 , 3 , 4 , 5 , 6 , 10 are referred in the literature as tyrosinase kinase inhibitors, in the treatment of schistosomiasis whereas 3 as a urease inhibitor. However their synthesis follow a different route from the described herein procedure [38,39,40,41,42,43,44,45,46,47,48,49,50,51].…”

Section: Introductionmentioning

confidence: 99%

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

2019

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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

2019

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“…Properly functionalized pyrazoles have appeared as HIV‐1 reverse transcriptase inhibitors [81] and sodium channel blockers [82] . Most widely used method for synthesis of 4,4 ’ ‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1 H ‐pyrazol‐5‐ol) involves the one‐pot combination of Knoevenagel‐Michael reaction of aldehydes with 3‐methyl‐1‐phenyl‐1 H ‐pyrazol‐5‐ol performed under different reaction conditions with a large range of catalysts, such as sodium dodecyl sulfate, [83] eletrocatalytic procedure, [84] SDBS, [85] silica‐SO 3 H, [86] PEG‐SO 3 H, [87] phosphomolybdic acid, [88] biosurfactant, [89] 3‐aminopropylatedsilica gel, [90] Caffein‐H 3 PO 4 , [91] 1,3‐disulfonic acid imidazolium tetrachloroaluminate [92] and metal complexes [93] . Recently, a number of protocol have been designed on this moiety [94] .…”

Section: Introductionmentioning

confidence: 99%

Humic acid: A Biodegradable Organocatalyst for Solvent‐free Synthesis of Bis(indolyl)methanes, Bis(pyrazolyl)methanes, Bis‐coumarins and Bis‐lawsones

Mitra

Ghosh

2021

ChemistrySelect

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Humic acid, a biodegradable, non‐toxic and easily accessible high molecular weight organocatalyst has been explored for the straightforward and environmentally benign approach towards the preparation of diverse array of functionalized bis(indolyl)methanes, bis(pyrazolyl)methanes, bis‐coumarins and bis‐lawsones by the reaction of a vast range of aldehydes with indole, 3‐methyl‐1‐phenyl pyrazolone, 4‐hydroxycoumarin and 2‐hydroxynaphthalene‐1,4‐dione respectively under solvent‐free condition. These protocols proceed without any hazardous solvents, toxic metal catalysts and harsh reaction conditions. In addition, low catalyst loading, good yield and excellent functional group tolerance are the key advantages of these protocols. The used catalyst and solvent‐free approach make this strategy safe to our mother earth. For the first time reusability of humic acid was investigated and found that it can be recycled up to fifth run without any significant loss of its activity at the end of the reaction. Some bioactive molecules such as arundine, trisindoline and vibribdole A were easily synthesized in our lab by utilizing this designed strategy.

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“…Hence, owing to the varied practical beneficial properties as therapeutic and curative agents in clinical applications, a great deal of attention of synthetic and medicinal chemists has been focused on the topic of the preparation of 4,4′‐(arylmethylene)bis(1 H –pyrazol‐5‐ol) derivatives and pyrano[3,2‐ c ]pyrazoles . Although a number of procedures have been reported for the synthesis of 4,4′‐(arylmethylene)bis(1 H –pyrazol‐5‐ol) derivatives and pyrano[3,2‐ c ]pyrazoles, all of the investigated methods suffer from one or more defects, including difficult‐to‐prepare catalysts, prolonged reaction times with low or moderate yields, employing toxic and hazardous organic solvents, harsh reaction conditions and tedious work‐up protocols.…”

Section: Introductionmentioning

confidence: 99%

Application of a biological‐based nanomagnetic catalyst in the synthesis of bis‐pyrazols and pyrano[3,2‐c]pyrazoles

Navazeni

Yarie

Ayazi‐Nasrabadi

2016

Applied Organom Chemis

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{Fe 3 O 4 @SiO 2 @(CH 2 ) 3 -thiourea dioxide-SO 3 H/HCl}, a newly reported nanomagnetic core-shell supported solid acid catalyst, was successfully employed in the preparation of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) and pyrano[3,2-c]pyrazole derivatives. The presented methods are very efficient and high-yielding. Also, the catalyst exhibited powerful potential for reusability in both types of reactions.

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Aqueous extract of Balanites roxburghii fruit: a green dispersant for C–C bond formation

Abstract: A natural dispersant exhibiting recyclable buffer property is obtained from aqueous extract of Balanites roxburghii fruit and used as a highly efficient catalytic medium for C–C bond construction via Knoevenagel condensation and tandem Knoevenagel–Michael reaction.

Cited by 22 publications

References 54 publications

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

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

Humic acid: A Biodegradable Organocatalyst for Solvent‐free Synthesis of Bis(indolyl)methanes, Bis(pyrazolyl)methanes, Bis‐coumarins and Bis‐lawsones

Application of a biological‐based nanomagnetic catalyst in the synthesis of bis‐pyrazols and pyrano[3,2‐c]pyrazoles

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