6415-59-4 Usage
Uses
Used in Pharmaceutical Applications:
SEDANOLIDE is used as a therapeutic agent for its potential cancer-preventive properties. It functions by inducing the expression of glutathione S-transferase, which aids in the detoxification of harmful substances and reduces the risk of chemical-induced carcinogenesis in mice.
Used in Anticancer Research:
In the field of cancer research, SEDANOLIDE is utilized as a compound of interest for its ability to potentially reduce the incidence of cancer. Its mechanism of action involves the induction of glutathione S-transferase, which may contribute to the prevention of carcinogenesis and the overall management of cancer risk.
Biological Activity
sedanolide is a natural compound produced in edible umbelliferous plants, such as celery seed oil [1].in hepg2 and caco-2 cells, treatment with sedanolide (7-500 μm) for 24h showed no effect on cell viability. in hepg2 cells cultured in sedanolide-free medium, sedanolide (500 μm) treatment for 72h decreased cell viability. pretreatment with sedanolide (100 μm) for 24 h and exposement to either h2o2 or tbooh did not exhibit statistically significant difference in viability from controls. in hepg2 following 24-h incubation with 500 μm sedanolide, a significant increase in dna strand breaks was observed. sedanolide did not modulate h2o2- and tbooh-induced dna damage. sedanolide was relatively nontoxic to cells in culture [1]. sedanolide (sn) possesses antioxidant effects. in human liver cancer (j5) cells, treatment with sedanolide suppressed j5 cell viability by inducing autophagy. sedanolide decreased protein expression levels of phosphoinositide 3-kinase (pi3k)-i, mammalian target of rapamycin (mtor) and akt and increased pi3k-iii, lc3-ii and beclin-1 protein levels. sedanolide increased the cytosolic phosphorylation of inhibitor of kappa b (iκb) and nuclear p65 and the dna-binding activity of nf-κb. sedanolide induced j5 cell autophagy by regulating pi3k, p53 and nf-κb autophagy-associated signaling pathways in j5 cells [2]. sedanolide (100 μg/ml) inhibited cyclooxygenases-1 and -2 at 250 pg/ml and blocked topoisomerase-i and-ii activity [3].
references
[1] woods j a, jewell c, o'brien n m. sedanolide, a natural phthalide from celery seed oil: effect on hydrogen peroxide and tert-butyl hydroperoxide-induced toxicity in hepg2 and caco-2 human cell lines[j]. in vitro & molecular toxicology: a journal of basic and applied research, 2001, 14(3): 233-240.[2] hsieh s l, chen c t, wang j j, et al. sedanolide induces autophagy through the pi3k, p53 and nf-κb signaling pathways in human liver cancer cells[j]. international journal of oncology, 2015, 47(6): 2240-2246[3] momin r a, nair m g. antioxidant, cyclooxygenase and topoisomerase inhibitory compounds from apium graveolens linn. seeds[j]. phytomedicine, 2002, 9(4): 312-318.
Check Digit Verification of cas no
The CAS Registry Mumber 6415-59-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,4,1 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 6415-59:
(6*6)+(5*4)+(4*1)+(3*5)+(2*5)+(1*9)=94
94 % 10 = 4
So 6415-59-4 is a valid CAS Registry Number.
InChI:InChI=1/C22H16ClN3OS2/c1-13-6-2-3-7-15(13)20(27)26-22(28)25-18-12-14(10-11-16(18)23)21-24-17-8-4-5-9-19(17)29-21/h2-12H,1H3,(H2,25,26,27,28)
6415-59-4Relevant academic research and scientific papers
Total syntheses of (±)-cis- and (±)-trans-neocnidilides
Mahadevegowda, Surendra H.,Khan, Faiz Ahmed
supporting information, p. 4400 - 4403 (2014/07/22)
Total syntheses of two antimicrobial natural products (±)-cis- neocnidilide and (±)-trans-neocnidilide starting from a readily preparable cyclohexa[b]-fused 5-oxabicyclo[2.1.1]hexane derivative are presented. The diastereomeric tetrahydrofuran tricarboxylate epimers obtained from a BF3·OEt2 promoted Grob-type fragmentation of the oxa-bicycle derivative were converted into title natural products by employing pyridinium dichromate/acetic anhydride mediated bis-oxidative cleavage reaction.
Synthesis and sensory evaluation of all stereoisomers of sedanolide
Oguro, Daichi,Watanabe, Hidenori
experimental part, p. 777 - 781 (2011/03/19)
Synthesis and sensory evaluation of all stereoisomers of sedanolide (1) are described. The asymmetric synthesis was achieved with using the all stereoisomers of bromoalcohol (3) prepared by enzymatic resolution and inversion of the secondary alcohol. All
Pentacovalent Oxaphosphorane Chemistry in Organic Synthesis. 2. Total Syntheses of (+/-)-trans- and (+/-)-cis-Neocnidilides
McClure, Cynthia K.,Jung, Kang-Yeoun
, p. 2326 - 2332 (2007/10/02)
Both (+/-)-trans- and (+/-)-cis-neocnidilides (1 and 2) have been synthesized via the route illustrated in Scheme III.The condensation of the 1,2λ5-oxaphospholene 5b with valeraldehyde produced the highly substituted phosphonates 12s and 12a, which were transformed via an intramolecular Wadsworth-Horner-Emmons olefination reaction to the title compounds.
