Related Experiment Video
Updated: Jul 22, 2025
09:56
Preparation and Characterization of Lipophilic Doxorubicin Pro-drug Micelles
Published on: August 2, 2016
15.0K
Potential anticancer and antioxidant lauric acid-based hydrazone synthesis and computational study toward the
Mohammed A Assiri1, Akbar Ali2, Muhammad Ibrahim3
1Chemistry Department, Faculty of Science, King Khalid University P.O. Box 9004 Abha 61413 Saudi Arabia.
RSC Advances
|July 21, 2023
Summary
Lauric acid-based hydrazones were synthesized and screened for anticancer and antioxidant properties. NBDH showed strong antioxidant activity, while FBDH demonstrated significant anticancer potential, indicating promising applications.
Area of Science:
- Synthetic organic chemistry
- Medicinal chemistry
- Computational chemistry
Background:
- Natural product modification is crucial for discovering new chemical entities with therapeutic potential.
- Lauric acid derivatives offer a versatile scaffold for developing novel bioactive compounds.
Purpose of the Study:
- To synthesize and characterize novel lauric acid-based hydrazones: (E)-N'-(2-nitrobenzylidene)dodecanehydrazide (NBDH), (E)-N'-(naphthalen-1-ylmethylene)dodecanehydrazide (NMDH), and (E)-N'-(4-fluorobenzylidene)dodecanehydrazide (FBDH).
- To evaluate the anticancer and antioxidant activities of the synthesized compounds.
- To perform comprehensive computational analyses to understand their reactivity and potential applications.
Main Methods:
- Synthesis and spectroscopic characterization (FT-IR, UV-Vis) of lauric acid-based hydrazones.
- In vitro screening for antioxidant activity using DPPH inhibition assay.
- In vitro screening for anticancer activity.
- Density Functional Theory (DFT) calculations including geometrical optimization, MEP, FMO, NBO, ELF, LOL, GRP, and NLO analysis at the B3LYP/6-311+G(d,p) level.
Main Results:
- NBDH exhibited the highest DPPH inhibitory activity, indicating potent antioxidant potential.
- FBDH demonstrated the highest anticancer activity, showing maximum percent viability.
- Computational analyses confirmed extended conjugation, intramolecular charge transfer, and significant potential for biological, electronic, and nonlinear optical (NLO) applications.
Conclusions:
- The synthesized lauric acid-based hydrazones possess significant antioxidant and anticancer properties.
- DFT calculations provide insights into the structure-activity relationships and confirm the potential for NLO applications.
- These compounds represent promising candidates for further development in medicinal and materials science.
Related Concept Videos
01:27Local Anesthetics: Chemistry and Structure-Activity Relationship
4.5K
Local anesthetics (LAs) are drugs that induce a temporary loss of sensation in a limited body area, preventing pain. Cocaine was the first local anesthetic discovered in the late 19th century. Cocaine is a benzoic acid ester obtained from the leaves of coca shrubs and was often used for its psychotropic effects. Cocaine was first isolated in 1860 by Albert Niemann. Sigmund Freud studied the physiological actions of cocaine. Carl Koller later introduced it into clinical practice in 1884 as a...
4.5K
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
8.5K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
8.5K
01:18Aromatic Hydrocarbon Anions: Structural Overview
2.8K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
Due to the absence of continuous...
2.8K
02:23Alcohols from Carbonyl Compounds: Reduction
10.5K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
10.5K
01:01Acid Halides to Carboxylic Acids: Hydrolysis
2.8K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
2.8K
02:36Regioselectivity and Stereochemistry of Hydroboration
8.2K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.2K