3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol

Base Information

• Chemical Name: 3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol
• CAS No.: 4449-51-8
• Molecular Formula: C27H41NO2
• Molecular Weight: 411.628
• Hs Code.: 29349990
• European Community (EC) Number: 628-058-8
• DSSTox Substance ID: DTXSID80859871
• Wikipedia: Cyclopamine
• Wikidata: Q105217576
• Metabolomics Workbench ID: 126905
• ChEMBL ID: CHEMBL2132004
• Mol file: 4449-51-8.mol

Synonyms:4449-51-8;3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol;HSDB 3505;C27-H41-N-O2;(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol;Veratraman-3-ol, 17,23-epoxy-, (3beta,23beta)-;Veratraman-3-ol, 17,23-epoxy-, (3.beta.,23.beta.)-;17,23-Epoxyveratraman-3-ol;Cyclopamine (11-Deoxyjervine);CHEMBL2132004;SCHEMBL10330892;DTXSID80859871;AKOS015842657;LS-15207;FT-0624245;A826604;3',6',10,11b-tetramethyl-3-spiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]ol

Chemical Property of 3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 236-238 °C
• Refractive Index: 1.583
• Boiling Point: 550.794 °C at 760 mmHg
• PKA: 15.05±0.70(Predicted)
• Flash Point: 286.91 °C
• PSA: 41.49000
• Density: 1.14 g/cm³
• LogP: 5.33070
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 411.313729551
• Heavy Atom Count: 30
• Complexity: 801

Purity/Quality:

98% ^*data from raw suppliers

Cyclopamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5CC4=C3C)C)O)C)NC1
• Description: Cyclopamine is a natural steroidal alkaloid that inhibits signaling through the hedgehog pathway at the level of the pathway activator Smoothened. By altering gene expression in this signaling sequence, cyclopamine induces defects in morphogenesis, first observed in chicks and sheep as cyclopia. As a readout of action, cyclopamine inhibits hedgehog-dependent expression of Pax7 with an IC50 value of 24 nM. Although teratogenic during development, cyclopamine has potential applications in the treatment of cancer.
• Uses: Has antibacterial properties. Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects of oncogenic mutations in Smoothened and Patched.1 Solubility: 1mg dissolves in 0.2ml DMSO with heating to approximately 70 degrees (ca. 12 mmol sol.) Solubility: 4mg dissolves in 1ml 95% Ethanol Cyclopamine antibacterial properties. Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects of oncogenic mutations in Smoothened and Patched. Cyclopamine, is used as a hedgehog [Hh] signaling pathway and Smo inhibitor. It depletes stem-like cancer cells in glioblastoma and blocks tumor engraftment. Can also be used to induce differentiation of human embryonic stem cells (hESCs) into hormone-expressing endocrine cells.

Technology Process of 3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol

There total 6 articles about 3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol 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: 91.0%

C33H45NO4S (1198184-95-0) → cyclopamine (4449-51-8)

Guidance literature:

C₃₃H₄₅NO₄S; With naphthalene; sodium; In 1,2-dimethoxyethane; at -78 ℃; for 3h; Inert atmosphere;

With water; sodium hydrogencarbonate; In 1,2-dimethoxyethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.200902520

Reference yield: 51.0%

jervine (469-59-0) → cyclopamine (4449-51-8)

Guidance literature:

With potassium hydroxide; hydrazine hydrate; Heating; 1.) triethylene glycol, 120 deg C, 1 h, 2.) triethylene glycol, 200 deg C, 3 h;

DOI:10.1246/bcsj.53.210

Reference yield:

cycloposine → cyclopamine (4449-51-8)

Guidance literature:

With water; 2-amino-2-hydroxymethyl-1,3-propanediol; In ethanol; dimethyl sulfoxide; at 37 ℃; for 22h; pH=7.2; pH-value; Reagent/catalyst; Solvent; Temperature; Enzymatic reaction;

upstream raw materials:

jervine

C₃₃H₄₅NO₄S

C₃₅H₄₆N₂O₇

Downstream raw materials:

C₄₈H₆₂N₂O₁₆

bis-CBz-cyclopamine

C₄₁H₅₇NO₅

C₄₄H₅₅NO₆

Refernces

• 1、 Ko Kaneko et al.. "". . p. 2497,2498 2500. Retrieved 1970.
• 2、 -. "Isolation of Cyclopamine". Paragraph 0115. . Retrieved 2016/07/05.
• 3、 Hamon, Florian,Renoux, Brigitte,Chadéneau, Corinne,Muller, Jean-Marc,Papot, Sébastien. "Study of a cyclopamine glucuronide prodrug for the selective chemotherapy of glioblastoma". experimental part. p. 1678 - 1682. Retrieved 2010/06/14.