Green Chemistry – Aspects for the Knoevenagel Reaction

Menegatti, Ricardo

doi:10.5772/36489

Cited by 13 publications

(9 citation statements)

References 55 publications

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“…Another reaction, the Knoevenagel condensation, involves benzaldehyde and malonic acid in the presence of a weak base ( e.g . pyridine), with subsequent acid hydrolysis . An exemplary modification of this method uses pyridine as a solvent and a catalyst, and β ‐alanine as a co‐catalyst .…”

Section: Introductionmentioning

confidence: 99%

Cinnamic acid derivatives in cosmetics: current use and future prospects

Gunia‐Krzyżak

Słoczyńska

Popiół

et al. 2018

Intern J of Cosmetic Sci

135

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Cinnamic acid derivatives are widely used in cosmetics and possess various functions. This group of compounds includes both naturally occurring and synthetic substances. On the basis of the Cosmetic Ingredient Database (CosIng) and available literature, this review summarizes their functions in cosmetics, including their physicochemical and biological properties as well as reported adverse effects. A perfuming function is typical of many derivatives of cinnamaldehyde, cinnamyl alcohol, dihydrocinnamyl alcohol and cinnamic acid itself; these substances are commonly used in cosmetics all over the world. Some of them show allergic and photoallergic potential, resulting in restrictions in maximum concentrations and/or a requirement to indicate the presence of some substances in the list of ingredients when their concentrations exceed certain fixed values in a cosmetic product. Another important function of cinnamic acid derivatives in cosmetics is UV protection. Ester derivatives such as ethylhexyl methoxycinnamate (octinoxate), isoamyl p-methoxycinnamte (amiloxiate), octocrylene and cinoxate are used in cosmetics all over the world as UV filters. However, their maximum concentrations in cosmetic products are restricted due to their adverse effects, which include contact and a photocontact allergies, phototoxic contact dermatitis, contact dermatitis, estrogenic modulation and generation of reactive oxygen species. Other rarely utilized functions of cinnamic acid derivatives are as an antioxidant, in skin conditioning, hair conditioning, as a tonic and in antimicrobial activities. Moreover, some currently investigated natural and synthetic derivatives of cinnamic acid have shown skin lightening and anti-ageing properties. Some of them may become new cosmetic ingredients in the future. In particular, 4-hydroxycinnamic acid, which is currently indexed as a skin-conditioning cosmetics ingredient, has been widely tested in vitro and in vivo as a new drug candidate for the treatment of hyperpigmentation.

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Section: Introductionmentioning

confidence: 99%

Cinnamic acid derivatives in cosmetics: current use and future prospects

Gunia‐Krzyżak

Słoczyńska

Popiół

et al. 2018

Intern J of Cosmetic Sci

135

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“…Because of its operational simplicity and expedited access to α,β-unsaturated motifs, the Knoevenagel condensation has found multiple applications in organic synthesis, including in industrial settings . One of its key features is the possibility to engage the resulting alkene in tandem processes, such as Michael, Diels–Alder, or sigmatropic reactions .…”

Section: Introductionmentioning

confidence: 99%

Room Temperature, Reductive Alkylation of Activated Methylene Compounds: Carbon–Carbon Bond Formation Driven by the Rhodium-Catalyzed Water–Gas Shift Reaction

2016

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The rhodium-catalyzed water−gas shift reaction has been demonstrated to drive the reductive alkylation of several classes of activated methylene compounds at room temperature. Under catalysis by rhodium trichloride (2−3 mol %), carbon monoxide (10 bar), water (2−50 equiv), and triethylamine (2.5−7 equiv), the scope has been successfully expanded to cover a wide range of alkylating agents, including aliphatic and aromatic aldehydes, as well as cyclic ketones, in moderate to high yields. This method is comparable to, and for certain aspects, surpasses the established reductive alkylation protocols.

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“…[30][31][32][33][34][35][36][37][38][39][40][41] Natural products like ajmalicine (1, antihypertensive alkaloid) and pharmaceuticals like AMG 837 (2, type II diabetes) and clinical agents such as atorvastatin (3, cardiovascular disease), lumefantrine (4, malaria) and sunitinib (5, gastrointestinal stromal tumor) are the representatives prepared by utilising Knoevenagel reaction (Figure 1). [17,[42][43][44] Dr. Ramya Tokala was born in Vijayawada, Andhra Pradesh, India, in 1991. The synthesis of these clinical agents emphasising the Knoevenagel reaction isis outlined in Scheme 3.…”

Section: Pharmaceutical Significance Of the Knoevenagel Reactionmentioning

confidence: 99%

Contribution of Knoevenagel Condensation Products toward the Development of Anticancer Agents: An Updated Review

2022

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Knoevenagel condensation is an entrenched, prevailing, prominent arsenal following greener principles in the generation of α, β-unsaturated ketones/carboxylic acids by involving carbonyl functionalities and active methylenes. This reaction has proved to be a major driving force in many multicomponent reactions indicating the prolific utility toward the development of biologically fascinating molecules. This eminent reaction was acclimatised on different pharmacophoric aldehydes (benzimidazole, β-carboline, phenanthrene, indole, imidazothiadiazole, pyrazole etc.) and active methylenes (oxindole, barbituric acid, Meldrum's acid, thiazolidinedione etc.) to generate the library of chemical compounds. Their potential was also explicit to understand the significance of functionalities involved, which thereby evoke further developments in drug discovery. Furthermore, most of these reaction products exhibited remarkable anticancer activity in nanomolar to micromolar ranges by targeting different cancer targets like DNA, microtubules, Topo-I/II, and kinases (PIM, PARP, NMP, p300/CBP) etc. This review underscores the efficiency of the Knoevenagel condensation explored in the past six-year to generate molecules of pharmacological interest, predominantly toward cancer. The present review also provides the aspects of structure-activity relationships, mode of action and docking study with possible interaction with the target protein.

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Green Chemistry – Aspects for the Knoevenagel Reaction

Cited by 13 publications

References 55 publications

Cinnamic acid derivatives in cosmetics: current use and future prospects

Cinnamic acid derivatives in cosmetics: current use and future prospects

Room Temperature, Reductive Alkylation of Activated Methylene Compounds: Carbon–Carbon Bond Formation Driven by the Rhodium-Catalyzed Water–Gas Shift Reaction

Contribution of Knoevenagel Condensation Products toward the Development of Anticancer Agents: An Updated Review

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