N-[2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxospiro[1,2,4,6,6a,6b,7,8,11,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-yl]ethyl]-6-(3-phenylpropanoylamino)hexanamide

Base Information

• Chemical Name: N-[2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxospiro[1,2,4,6,6a,6b,7,8,11,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-yl]ethyl]-6-(3-phenylpropanoylamino)hexanamide
• CAS No.: 306387-90-6
• Molecular Formula: C₄₄H₆₃N₃O₄
• Molecular Weight: 698.002
• DSSTox Substance ID: DTXSID70587893
• Pharos Ligand ID: Z6H2NP4NWCFZ
• Mol file: 306387-90-6.mol

Synonyms:3-keto-N-aminoethylaminoethylcaproyldihydrocinnamoyl cyclopamine;KAAD-cyclopamine

Chemical Property of N-[2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxospiro[1,2,4,6,6a,6b,7,8,11,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-yl]ethyl]-6-(3-phenylpropanoylamino)hexanamide

Chemical Property:

• Boiling Point: 875.6oC at 760 mmHg
• PKA: 16.10±0.46(Predicted)
• Flash Point: 483.3oC
• PSA: 101.73000
• Density: 1.15g/cm3
• LogP: 8.40240
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 697.48185750
• Heavy Atom Count: 51
• Complexity: 1370

Purity/Quality:

3-Keto-N-aminoethyl-N’-aminocaproyldihydrocinnamoylCyclopamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(=O)CCC6(C5CC4=C3C)C)C)N(C1)CCNC(=O)CCCCCNC(=O)CCC7=CC=CC=C7
• Isomeric SMILES: C[C@@H]1C2[C@@H](CC(CN2CCNC(=O)CCCCCNC(=O)CCC3=CC=CC=C3)C)OC14CCC5C6CC=C7CC(=O)CCC7(C6CC5=C4C)C
• Uses: Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects ofoncogenic mutations in Smoothened and Patched.1 The KAAD derivative has shown 10-20 fold higher potency than cyclopamine in inhibition of ?-Galactosidase expression i Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects of oncogenic mutations in Smoothened and Patched.1 The KAAD-Cyclopamine has shown 10-20 fold higher potency than cyclopamine in inhibition of ?-Galactosidase expression in p2Ptch-1- cells, with similar or lower toxicity.KAAD-Cyclopamine compound is unstable in solution.

Technology Process of N-[2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxospiro[1,2,4,6,6a,6b,7,8,11,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-yl]ethyl]-6-(3-phenylpropanoylamino)hexanamide

There total 1 articles about N-[2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxospiro[1,2,4,6,6a,6b,7,8,11,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-yl]ethyl]-6-(3-phenylpropanoylamino)hexanamide 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: 87.0%

KAAD-Cyclopamine → 3-keto, N-(N'-(N-dihydrocinnamoylaminocaproyl)aminoethyl)cyclopamine (306387-90-6)

Guidance literature:

KAAD-Cyclopamine; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.666667h;

With triethylamine; In dichloromethane; at -78 - 20 ℃;