. Author manuscript; available in PMC: 2015 Dec 3.

Published in final edited form as: J Med Chem. 2014 Dec 16;58(2):665–681. doi: 10.1021/jm501165d

Table 3.

Comparison of Side Chain Dihedral Values for Global Minimum Energy Conformers and Binding Affinities (K_i) of Key Analogues

side chain dihedral	Ki = 0.5 nM (rCB1), = 0.8 nM (mCB2) (deg)		K_i = 0.9 nM (rCB1), = 1.4 nM (mCB2) (deg)	K_i = 47.6 nM (rCB1), = 39.3 nM (mCB2) (deg)
side chain dihedral	10a	no int H-bond 10a	(−)-Δ⁸-THC-DMH	(−)-Δ⁸-THC
C2–C3–C1′–C2′	−38.3	−54.5	−52.3	−85.6
C3–C1′–C2′–(C3′, O3′)	−60.2	−68.7	−60.0	179.9
C1′–C2′–(C3′, O3′)–C4′	174.6	176.1	175.2	−179.9
C2′–(C3′, O3′)–C4′–C5′	−164.7	−174.5	179.5	180.0
(C3′, O3′)–C4′–C5′–C6′	54.4	61.4	179.1
C4′–C5′–C6′–C7′	54.3	179.1	180.0