Sicanina

Base Information

• Chemical Name: Sicanina
• CAS No.: 22733-60-4
• Molecular Formula: C₂₂H₃₀O₃
• Molecular Weight: 342.478
• NSC Number: 135048
• DSSTox Substance ID: DTXSID20860284
• ChEMBL ID: CHEMBL1416486
• Mol file: 22733-60-4.mol

Synonyms:22733-60-4;Siccanin (TN);NSC135048;NCGC00181099-01;4,4,6a,9-Tetramethyl-1,2,3,4,4a,5,6,6a,11b,13b-decahydrobenzo[a]furo[2,3,4-mn]xanthen-11-ol;SCHEMBL3064856;CHEMBL1416486;DTXSID20860284;NCI60_000788;(13aS)-1,3,4,4a.beta.,5,6,6a,11b.beta.,13b.beta.-Decahydro-4,4,6a.beta.,9-tetramethyl-13H-benzo[a]furo[2,3,4-mn]xanthen-11-ol;(4R)-8,12,16,16-Tetramethyl-3,11-dioxapentacyclo[10.7.1.01,15.04,20.05,10]icosa-5,7,9-trien-6-ol;13H-Benzo[a]furo[2,4-mn]xanthen-11-ol, 1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-;13H-Benzo[a]furo[2,4-mn]xanthen-11-ol, 1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-, [4aS-(4a.alpha.,6a.alpha.,11b.alpha.,13aR*,13b.alpha.)]-;4,4,6a,9-Tetramethyl-1,2,3,4,4a,5,6,6a,11b,13b-decahydro-13H-benzo[a]furo[2,3,4-mn]xanthen-11-ol

Chemical Property of Sicanina

Chemical Property:

• Vapor Pressure: 6.41E-08mmHg at 25°C
• Melting Point: 139-140°
• Boiling Point: 427.8°Cat760mmHg
• PKA: 10.9(at 25℃)
• Flash Point: 212.5°C
• PSA: 38.69000
• Density: 1.18g/cm³
• LogP: 5.14570
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 342.21949481
• Heavy Atom Count: 25
• Complexity: 560

Purity/Quality:

95-99% ^*data from raw suppliers

Siccanin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C2C3C4C(CCC5C4(CCCC5(C)C)CO3)(OC2=C1)C)O
• 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: 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. Siccanin is an antifungal and SDHB (IP) inhibitor.

Technology Process of Sicanina

There total 41 articles about Sicanina which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

(-)-siccanin methyl ether (35477-60-2) → siccanin (22733-60-4)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200351868

Reference yield: 78.0%

siccanochromene E methyl ether (35477-60-2,36871-15-5,78341-70-5,123539-96-8) → (+/-)-siccanin (22733-60-4,78341-69-2,123539-95-7)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1021/ja00399a062

Reference yield:

8aα-methoxymethyl-5,5-dimethyl-4aα,5,6,7,8,8a-hexahydro-2(1H)-naphthalenone (78412-85-8,135163-81-4) → (+/-)-siccanin (22733-60-4,78341-69-2,123539-95-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) (i-Pr)2NLi / 1.) DME, -78 deg C

2: 100 percent / H₂ / Pd-C / ethanol

3: 89 percent / pyridinium tosylate / CH₂Cl₂

4: 99 percent / diethyl ether

5: 90 percent / PPTS, aq.EtOH / 60 °C

6: 80 percent / PCC / CH₂Cl₂

7: 1.) Li / 2.) DME, -75 -> 0 deg C

8: 78 percent / pyridinium chloride / CH₂Cl₂ / 0.5 h / 25 °C

9: 87 percent / NaSEt / dimethylformamide / 100 °C

10: 21 percent / conc.H₂SO₄ / various solvent(s) / 25 °C

11: BF₃*OEt₂ / CH₂Cl₂ / 25 °C

12: 78 percent / NaSEt / dimethylformamide / 100 °C

With ethanol; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; pyridine hydrochloride; pyridinium p-toluenesulfonate; lithium; pyridinium chlorochromate; lithium diisopropyl amide; sodium thioethylate; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00399a062

upstream raw materials:

(-)-siccanin methyl ether

(-)-siccanochromene methyl ether

(S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol

(S)-(-)-2,2-dimethyl-6-methylene-1-[1'-(phenylthio)methyl]cyclohexane

Refernces

• 1、 Trost, Barry M.,Shen, Hong C.,Surivet, Jean-Philippe. "An enantioselective biomimetic total synthesis of (-)-siccanin". . p. 3943 - 3947. Retrieved 2007/10/03.
• 2、 Kato, Michiharu,Heima, Kiyoshi,Matsumura, Yukio,Yoshikoshi, Akira. "Total Synthesis of Racemic Siccanin". . p. 2434 - 2435. Retrieved 2007/10/02.