22733-60-4 Usage
Description
Siccanin is an inhibitor of mitochondrial complex II (succinate dehydrogenase; IC50s = 0.87 and 9.3 μM for P. aeruginosa and rat mitochondria, respectively). It inhibits the growth of T. mentagrophytes (IC50 = 0.3 μg/ml) via inhibition of succinate oxidation in the mitochondria. It also inhibits the growth of C. albicans strains with IC50 values ranging from 5-40 and 80-90 μg/ml for aerobic and anaerobic conditions, respectively.
Uses
Different sources of media describe the Uses of 22733-60-4 differently. You can refer to the following data:
1. Siccanin is an unusual, fused, phenolic pentacycle first isolated from Helminthosporium siccans and reported in 1962 as a potent antifungal agent. Siccanin inhibits succinate dehydrogenase in the terminal electron transport system. More recent studies note the proximity of the siccanin binding site to the quinone-binding site of the enzyme. Species-selective inhibition by siccanin is unique among succinate dehydrogenase inhibitors and offers a lead for new chemotherapeutics.
2. Siccanin is an antifungal and SDHB (IP) inhibitor.
Check Digit Verification of cas no
The CAS Registry Mumber 22733-60-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,7,3 and 3 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 22733-60:
(7*2)+(6*2)+(5*7)+(4*3)+(3*3)+(2*6)+(1*0)=94
94 % 10 = 4
So 22733-60-4 is a valid CAS Registry Number.
InChI:InChI=1/C22H30O3/c1-13-10-14(23)17-15(11-13)25-21(4)9-6-16-20(2,3)7-5-8-22(16)12-24-18(17)19(21)22/h10-11,16,18-19,23H,5-9,12H2,1-4H3/t16?,18-,19?,21?,22?/m0/s1
22733-60-4Relevant articles and documents
Biomimetic enantioselective total synthesis of (-)-siccanin via the Pd-catalyzed asymmetric allylic alkylation (AAA) and sequential radical cyclizations
Trost, Barry M.,Shen, Hong C.,Surivet, Jean-Philippe
, p. 12565 - 12579 (2007/10/03)
(-)-Siccanin (1), a natural product possessing significant antifungal properties, was synthesized enantioselectively via a biomimetic route. This synthetic route features two sequential radical cyclizations: a Ti(III)-mediated radical cyclization of epoxy
Total Synthesis of dl-Siccanin and dl-Siccanochromene E
Kato, Michiharu,Matsumura, Yukio,Heima, Kiyoshi,Fukamiya, Narihiko,Kabuto, Chizuko,Yoshikoshi, Akira
, p. 711 - 722 (2007/10/02)
The stereoselective synthesis of dl-siccanin (1) and dl-siccanochromene E (2) has been described.Acid isomerization of nonconjugated octalone 11a, derived from known octalone 5, stereoselectively provided cis-fused octalone 12, from which cis-drimane alde
