22733-60-4 Usage
Description
Siccanin is an unusual, fused, phenolic pentacycle first isolated from Helminthosporium siccans and reported in 1962 as a potent antifungal agent. It is an inhibitor of mitochondrial complex II (succinate dehydrogenase) and has unique species-selective inhibition properties, making it a promising candidate for new chemotherapeutics.
Uses
Used in Antifungal Applications:
Siccanin is used as an antifungal agent for inhibiting the growth of various fungal species, such as T. mentagrophytes and C. albicans strains. It achieves this by inhibiting succinate oxidation in the mitochondria, with IC50 values ranging from 0.3 μg/ml to 90 μg/ml depending on the species and growth conditions.
Used in Drug Development:
Siccanin is used as a lead compound in the development of new chemotherapeutics due to its unique species-selective inhibition of succinate dehydrogenase. Its proximity to the quinone-binding site of the enzyme offers potential for designing more effective and targeted treatments.
Used in Research:
Siccanin is used in research to study the function and inhibition of succinate dehydrogenase in the terminal electron transport system. Its unique binding properties provide valuable insights into the development of novel inhibitors and understanding the underlying mechanisms of action.
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
