US 12,084,456 B2
Isocarbostyril alkaloids and functionalization thereof
David Sarlah, Champaign, IL (US); Tanner W. Bingham, Urbana, IL (US); and Lucas William Hernandez, Urbana, IL (US)
Assigned to The Board of Trustees of the University Of Illinois, Urbana, IL (US)
Appl. No. 17/299,365
Filed by The Board of Trustees of the University of Illinois, Urbana, IL (US)
PCT Filed Dec. 4, 2019, PCT No. PCT/US2019/064388
§ 371(c)(1), (2) Date Jun. 3, 2021,
PCT Pub. No. WO2020/117894, PCT Pub. Date Jun. 11, 2020.
Claims priority of provisional application 62/775,521, filed on Dec. 5, 2018.
Prior Publication US 2022/0064176 A1, Mar. 3, 2022
Int. Cl. C07D 491/056 (2006.01); B01J 31/22 (2006.01)
CPC C07D 491/056 (2013.01) [B01J 31/22 (2013.01); B01J 2531/16 (2013.01)] 21 Claims
 
1. An alkaloid compound of Formula I:

OG Complex Work Unit Chemistry
or a deuterium isotope thereof;
wherein
C is an sp3 carbon atom;
custom characteris a single bond, or an optional double bond wherein two adjacent custom character do not form consecutive double bonds;
Q1 is NRyRz, ORy, or SRy, wherein Rz is H or —(C1-C6)alkyl, and Ry is H, —(C1-C6)alkyl, or absent when custom character on Q1 is a double bond;
each Q2 is independently halo, —(C1-C6)alkyl, N(Ra)2, ORa, SRa, wherein each Ra is independently H or —(C1-C6)alkyl, or two adjacent Q2 optionally taken together form a ring;
m is 0-3;
R1 is halo, —(C1-C6)alkyl, —(C3-C6)cycloalkyl, SRb, —C(═O)Rc, —S(═O)2Rc, cyano, nitro, phenyl, N(Rb)2, or a nitrogen heterocycle; or
R1 and Q1 taken together form a 5- or 6-membered ring;
wherein
each Rb is independently H, —(C1-C6)alkyl, —C(═O)Rc, or optionally two Rb taken together form a heterocycle when R1 is N(Rb)2; and
Rc is H, OH, —(C1-C6)alkyl, —O(C1-C6)alkyl, N(Rd)2, or phenyl, wherein
each Rd is independently H or —(C1-C6)alkyl; and
each R2 is independently H, halo, or ORe wherein each Re is independently H, —(C1-C6)alkyl, or a protecting group, or two adjacent R2 taken together optionally form an epoxide, or an alkylenedioxy group;
R3 is H, —(C1-C6)alkyl, or —C(═O)Rc; and
wherein each —(C1-C6)alkyl, —(C3-C6)cycloalkyl, phenyl and heterocycle are optionally substituted with or one or more substituents, each —(C1-C6)alkyl and —(C3-C6)cycloalkyl is saturated or optionally unsaturated, and each —(C1-C6)alkyl is unbranched or optionally branched.