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. Author manuscript; available in PMC: 2020 Aug 21.
Published in final edited form as: J Med Chem. 2019 Jul 25;62(15):6958–6971. doi: 10.1021/acs.jmedchem.9b00339

Table 1.

Anti-HIV Replication Activities of GM Derivatives

graphic file with name nihms-1618681-t0009.jpg
compd R1 R2 R3 R4 R5 15,16 anti-HIV IC50
(nM)		 cytotoxicity
CC50 (nM)
1 OBz OH OH OH OBz C═CH2 0.13 ± 0.04 >1
2 OBz OAc OAc OAc OBz C═CH2 >1 >1
3 OBz OH OBz OBz OBz C═CH2 >1 >1
4 OH OH OH OH OH C═CH2 >1 >1
5 OH OH OH OH OBz C═CH2 >1 >1
6 OBz OH OH OH OBz CH─CH3 0.18 ± 0.05 >1
9a OBz OH OH ═O OBz C═CH2 0.14 ± 0.08 >1
9b OBz OH OH OAc OBz C═CH2 0.09 ± 0.04 >1
9c OBz OH OH tigloxy OBz C═CH2 >1 >1
9d OBz OH OH OBz OBz C═CH2 >1 >1
9e OBz OH OH O-4–methoxybenzoyl OBz C═CH2 >1 >1
9f OBz OH OH O-4–nitrobenzoyl OBz C═CH2 >1 >1
9g OBz OH OH O-trans-cinnamoyl OBz C═CH2 >1 >1
9h OBz OH OH O-2-naphthoyl OBz C═CH2 >1 >1
13a O-4-methoxybenzoyl OH OH OH OBz C═CH2 0.17 ± 0.04 >1
13b O-4-nitrobenzoyl OH OH OH OBz C═CH2 0.22 ± 0.05 >1
13c O-trans-cinnamoyl OH OH OH OBz C═CH2 >1 >1
13d O-2-naphthoyl OH OH OH OBz C═CH2 0.15 ± 0.03 >1
13e O-4-pyridinylcarbonyl OH OH OH OBz C═CH2 0.36 ± 0.09 >1
15a OBz OBz OH OH OBz C═CH2 >1 >1
15b OBz ═O OH OH OBz C═CH2 >1 >1
18 OBz OAc OH OH OBz C═CH2 >1 >1
19a OBz OH OAc OH OBz C═CH2 >1 >1
19b OBz OH OBz OH OBz C═CH2 >1 >1
19c OBz OH succinoxy OH OBz C═CH2 >1 >1
19d OBz OH 2,2-dimethylsuccinoxy OH OBz C═CH2 >1 >1
19e OBz OH 3,3-dimethylsuccinoxy OH OBz C═CH2 >1 >1
19f OBz OH O-camphanoyl OH OBz C═CH2 >1 >1
19g OBz OH O-2,2,5-trimethyl-1,3-dioxane-5-carboxyl OH OBz C═CH2 >1 >1
19h OBz OH O-trans-4-methoxycinnamoyl OH OBz C═CH2 >1 >1