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. Author manuscript; available in PMC: 2022 Feb 25.
Published in final edited form as: J Med Chem. 2020 Nov 17;63(23):14951–14978. doi: 10.1021/acs.jmedchem.0c01464

Table 3.

Reaction of Cysteamine with α-Methylene-γ-lactams.

graphic file with name nihms-1776635-t0014.jpg
Entry SM R1, R2 13Cβ ppm Half-life
1 45 Ph, H 115.3 2.1 da
2 49 Ph, Ph 117.1 2.1 d
3 51 Ph, 4-CF3-C6H4 118.2 9.8 h
4 52 Ph, 4-OMe-C6H4 116.7 8.5 d
5 54 Ph, Ts 121.4 <10 mina,b
6 60 H, Ac 120.6 5 min
7 S17 120.7 7 min
8 PTL 121.1c <5 mind

Conditions: HSCH2CH2NH2 (15 equiv), CDCl3 (0.006 M), rt

a

Reaction was performed with cysteamine that was ~60% oxidized

b

Reaction was complete at this time point

c

Based on previous literature.44

d

Based on previous literature.42