A Check on the Completeness of OSM Series 3 Compounds in Master List

[mattodd]

Drafting of this Issue is complete. It is now being verified

In advance of the first OSM Series 3 publication, I'm making a check on the accuracy of the analog page on the wiki vs the OSM Master List (ML). While this is underway, I've sorted the Master List according to Series Number and am "greening" entries that check out correctly.

1. OSM-E-23 (TF 8-1), OSM-E-24 (TF 16-1) and OSM E-26 (TF 4-1) had structures in the ML that lacked a double bond in the phenyl ring carrying the sulfonamide. These have been corrected. Example below.

2. A likely trivial structural error in the wiki pic for OSM-S-156 with a misplaced oxygen. Corrected to the diester in the wiki pic (which is the string already in the ML).

3. OSM-E-34 identical to OSM-S-488. The latter has incorrect strings in ML, again lacking double bond in phenyl ring. Now fixed.

4. OSM-S-490 was lacking a methyl on the boronate in the ML. Fixed.

5. The code OSM-S-486 had, in the wiki diagrams, been assigned to O=S(N)(C1=CC=CC(B2OC(C)(C(C)(O2)C)C)=C1)=O i.e. 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide, or the meta-boronate of phenylsulfonamide. However, this OSM code has also been assigned to a Series 4 compound. Given that the boronate is commercially available, the 486 code can remain assigned to the Series 4 compound and the structure has been removed from the wiki diagrams.

6. OSM-S-117, OSM-S-64 and OSM-S-493 are identical. Currently highlighted red and not yet fixed.

7. OSM-S-74 was listed in the Master List without a potency (in a column that appears to have lost its heading - there is only a "0" in the header now). In the original chemdraw it is shown with a potency of 17.6 uM. I have inserted this 17.6 uM figure back in the Master List, but this will need checking.

8. OSM-S-80 is listed in the Master List as having a potency of 70% at 40 uM, but in the chemdraw it's 80% at 40 uM. A small disparity, but needs checking.

9. There is a structural mismatch between Master List and Chemdraw for OSM-S-72. Which isomer is correct?

10. There are some compounds in the Tested sheet that I'm pretty sure were tested but which lack potency data in the Master List, and these need checking:
    OSM-S-435 (AEW108)
    OSM-S-454 (MNR117)
    OSM-S-453 (AT23) - need to establish if made.
    OSM-S-451 (AT5)
    OSM-S-456 (MNR110-1) - need to establish if made.
    OSM-S-452 (AT12) - need to establish if made.
    OSM-S-457 (MNR111) - need to establish if made.
    OSM-S-449 (MNR116)

[mattodd]

Hi @yinuowang0812.

The relevant files being discussed are here. The two chemdraws of interest are "S3 Synthesised and tested v4" and "S3 Synthesised and not tested".

Can you please check:

1. That the data in the two chemdraw sheets match what is in the Master List? i.e. that the code and structure match. Don't change anything in the Master List without noting the change you made (on this page).

2. That the above problems are indeed real problems and need sorting (you don't need to sort them - e.g. for problem number 10 I just need you to check that the compounds lack data. I don't need you to find the data)

Thank you!

[yinuowang0812]

Continued code and structure checking are going and will update here when I finish

The above problems have been sorted.

Master list updated:

1. the potency of OSM-S-80 has been corrected to 80% at 40 uM
2. OSM-S-72 SMILES code updated to O=S(NC1=C2SC(C3=CC=CC=C3)=CC2=NC=N1)(C4=CC=CC=C4)=O from O=S(NC1=C2C(SC(C3=CC=CC=C3)=C2)=NC=N1)(C4=CC=CC=C4)=O

Chemdraw updated:

1. OSM-S-117, OSM-S-64 and OSM-S-493 are identical so I keep the oldest version OSM-S-64 as the series name.

The compounds in the Tested sheet but lack data (confirm):

OSM-S-435 (AEW108)
OSM-S-454 (MNR117)
OSM-S-453 (AT23)
OSM-S-451 (AT5)
OSM-S-456 (MNR110-1)
OSM-S-452 (AT12)
OSM-S-457 (MNR111)
OSM-S-449 (MNR116)