Ethanol → 6-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)cyclopropyl)-3-pyridinecarboxylic acid

HRID 2115162Notes

Reaction equation

HRID 2115162 reaction equation
C[C@]12[C@]3(C)CC[C@H]4C(C)(C)C(=O)C([C:28]#[N:29])=C[C@]4(C)C3=CC(=O)[C@@H]1[C@H]1[C@](C(O)=O)(CCC(C)(C)C1)CC2.C[C@]12[C@]3(C)CC[C@H]4C(C)(C)C(=O)C(C#N)=C[C@]4(C)C3=CC(=O)[C@@H]1[C@H:46]1[C@:41]([C:70](OC)=O)([CH2:42][CH2:43][C:44]([CH3:69])([CH3:68])[CH2:45]1)[CH2:40][CH2:39]2.CC1CCCC(C)(C)C=1/[CH:83]=[CH:84]/[C:85](/[CH3:95])=[CH:86]/[CH:87]=[CH:88]/[C:89](/C)=[CH:90]/[C:91]([OH:93])=[O:92].[CH2:96](O)[CH3:97]>CS(C)=O>[CH3:83][C:84]1[CH:39]=[C:40]2[C:41]([CH3:70])([CH3:42])[CH2:46][CH2:45][C:44]([CH3:69])([CH3:68])[C:43]2=[CH:95][C:85]=1[C:86]1([C:87]2[CH:88]=[CH:89][C:90]([C:91]([OH:93])=[O:92])=[CH:28][N:29]=2)[CH2:97][CH2:96]1

Participants

6

Reactant 4

HCID 702EthanolHCID 400010BardoxoloneHCID 400769Bardoxolone MethylHCID 444795Retinoic Acid

Product 1

HCID 39226-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)cyclopropyl)-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Reagents. Stock solutions of CDDO and/or CDDO-Me at 10 mM in DMSO were stored at −20° C. Working solutions were prepared in DMSO and added directly to culture medium. ATRA was purchased from Sigma Chemical Co. (St. Louis, Mo.) and kept in 100% ethanol solution at −20° C. RXR-specific ligand LG-100268 was kindly provided by Dr. Richard Heyman. Caspase-3 inhibitor Z-DEVD-fmk and bongkrekic acid (BA) were obtained from Calbiochem (La Jolla, Calif.). Cyclosporin A (CyA) was purchased from Sandoz. Fas-signaling antibody CH11 and Fas-blocking antibody ZB4 were obtained from Immunotech (Miami, Fla.).

Workup

  1. customwere stored at −20° C
  2. additionadded directly to culture medium

Sources & evidence

ORD record
ord-b45adcc08b6c4c37a67d8aa3725ea976
Source dataset
uspto-grants-2008_10
Patent number
US07435755B2

Reaction notes

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