63177-57-1

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2,5-DIHYDROXYCINNAMATE is used as an inhibitor of the EGF receptor associated tyrosine kinase for its ability to interfere with the activity of this enzyme, which plays a crucial role in cell signaling and proliferation. By inhibiting this kinase, METHYL 2,5-DIHYDROXYCINNAMATE can potentially be employed in the development of therapeutic strategies against various diseases, including cancer.
Used in Biochemical Research:
As a stable Erbstatin analogue, METHYL 2,5-DIHYDROXYCINNAMATE is used to inhibit tyrosine kinase. It has been shown to delay the S-phase induction by epidermal growth factor in quiescent normal rat kidney cells, without affecting the total amount of DNA synthesis. This property makes it a valuable tool in studying the mechanisms of cell cycle regulation and the role of tyrosine kinase in cellular processes.

InChI:InChI=1/C10H10O4/c1-14-10(13)5-2-7-6-8(11)3-4-9(7)12/h2-6,11-12H,1H3/b5-2+

Upstream product

• 1194-98-5 2,5-Dihydroxybenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 3943-97-3 methyl 4-hydroxycinnamate 

Downstream Products

• 116406-20-3 Methyl (E)-3-(2,5-Dimethoxyphenyl)propenoate 

Relevant academic research and scientific papers

Antioxidant-Inspired Drug Discovery: Antitumor Metabolite Is Formed in Situ from a Hydroxycinnamic Acid Derivative upon Free-Radical Scavenging

Cancer cells generally possess higher levels of reactive oxygen species than normal cells, and this can serve as a possible therapeutic target. In this proof-of-concept study, an antioxidant-inspired drug discovery strategy was evaluated using a hydroxycinnamic acid derivative. The processing of oxidized mixtures of p-coumaric acid methyl ester (pcm) revealed a new antitumor lead, graviquinone. Graviquinone bypassed ABCB1-mediated resistance, induced DNA damage in lung carcinoma cells but exerted DNA protective activity in normal keratinocytes, and modulated DNA damage response in MCF-7 cells. The cytotoxic effect of pcm in MCF-7 cells was potentiated under H2O2-induced oxidative stress, and the formation of graviquinone was confirmed by Fenton's reaction on pcm. In silico density functional theory calculations suggested graviquinone as a kinetic product of pcm-scavenging ?OH radicals. Our results demonstrate the pharmacological value of an in situ-formed, oxidative stress-related metabolite of an antioxidant. This might be of particular importance for designing new strategies for antioxidant-based drug discovery.

A biomimetic total synthesis of allomicrophyllone: Protective Diels-Alder reaction as a stratagem

A biomimetic total synthesis of bioactive tetracyclic natural product allomicrophyllone has been achieved in which a protective Diels-Alder reaction employing a disposable sacrificial 1,3-diene directs the regioselectivity of the subsequent Diels-Alder re

Syntheses of certain 3-aryl-2-propenoates and evaluation of their cytotoxicity

A series of 3-aryl-2-propenoates including cinnamates, (E)-methyl/ethyl 3-[2-(1,4-dimethoxy-5,8-dione)naphthalenyl]-2-propenoates (8ba, 8bb) and (E)-methyl/ethyl 3-[2-(1,4-dihydroxy-9,10-dione)anthracenyl]-2-propenoates (9aa, 9ab) was synthesized and eval