Estriol → Estriol

HRID 1709965Notes

Reaction equation

HRID 1709965 reaction equation
[CH3:1][C@@:2]12[C@@H:18]([OH:19])[C@H:17]([OH:20])[CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:21])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[CH3:22][C@@:23]12[C:39](=[O:40])[CH2:38][CH2:37][C@H:36]1[C@H:35]1[C@@H:26]([C:27]3[CH:28]=[CH:29][C:30]([OH:41])=[CH:31][C:32]=3[CH2:33][CH2:34]1)[CH2:25][CH2:24]2.C[C@@]12[C@@H]([OH:60])CC[C@H]1[C@H]1[C@@H](C3C=CC(O)=CC=3CC1)CC2>>[CH3:1][C@@:2]12[C@@H:18]([OH:19])[C@H:17]([OH:20])[CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:21])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[CH3:22][C@@:23]12[C@@H:39]([OH:40])[CH2:38][CH2:37][C@H:36]1[C@H:35]1[C@@H:26]([C:27]3[CH:28]=[CH:29][C:30]([OH:41])=[CH:31][C:32]=3[CH2:33][CH2:34]1)[CH2:25][CH2:24]2.[CH3:1][C@@:2]12[C@@H:18]([OH:19])[C@H:17]([OH:20])[CH2:16][C@H:15]1[C@@H:14]1[CH2:13][C:12]([C:11]3[CH:10]=[C:9]([OH:21])[CH:8]=[CH:7][C:6]=3[C@H:5]1[CH2:4][CH2:3]2)=[O:60]

Participants

6

Reactant 3

HCID 5756EstriolHCID 5757EstradiolHCID 5870Estrone

Product 3

HCID 5756EstriolHCID 5757EstradiolHCID 118769596-Ketoestriol

Procedure

A series of estriol and estradiol derivatives was prepared by Walker et al.. Steroids. Volume 21, 259-283 (1973) with substituents at the 6-position. These specific 6-oxo derivatives were used to prepare immunogens with carrier proteins and were compared with randomly linked derivatives for their ability to elicit antibodies with minimal cross-reactivity with structurally similar analogs. It was found that random-linkage immunogens of estriol chloroformates with carrier proteins produced antibodies with 30-100% cross-reactivity, while those with a 6-oxo linked estriol had a 1-12% cross-reactivity with estrone and estradiol. This study suggests that linkage through the 6-position led to immunogens capable of producing antibodies with acceptable specificity However, each derivative required extensive complex synthetic procedures for its preparation, diminishing their convenience and utility in the preparation of immunogens; 6-oxoestriol itself was only produced in 11% yield.

Workup

  1. customto prepare immunogens with carrier proteins
  2. customproduced antibodies with 30-100% cross-reactivity
  3. customeach derivative required extensive complex synthetic procedures for its preparation
  4. customin the preparation of immunogens

Sources & evidence

ORD record
ord-ac8f366ea5f84ee6842e7742906bb8f4
Source dataset
uspto-grants-1990_08
Patent number
US04952569

Reaction notes

Loading…