US 12,344,594 B2
Red-shifted fluorophores
Luke D. Lavis, Leesburg, VA (US); and Jonathan B. Grimm, Ashburn, VA (US)
Assigned to HOWARD HUGHES MEDICAL INSTITUTE, Chevy Chase, MD (US)
Filed by HOWARD HUGHES MEDICAL INSTITUTE, Chevy Chase, MD (US)
Filed on Dec. 9, 2020, as Appl. No. 17/116,987.
Claims priority of provisional application 62/945,295, filed on Dec. 9, 2019.
Prior Publication US 2021/0171490 A1, Jun. 10, 2021
Int. Cl. C07D 311/82 (2006.01); C07C 63/72 (2006.01); C07D 335/12 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 413/10 (2006.01); C07D 491/147 (2006.01); C07F 7/08 (2006.01); C07F 9/6568 (2006.01); G01N 21/64 (2006.01)
CPC C07D 311/82 (2013.01) [C07C 63/72 (2013.01); C07D 335/12 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 413/10 (2013.01); C07D 491/147 (2013.01); C07F 7/0816 (2013.01); C07F 9/65685 (2013.01); G01N 21/6428 (2013.01); G01N 21/6458 (2013.01); G01N 2201/06193 (2013.01)] 35 Claims
 
1. A compound of the following structure:

OG Complex Work Unit Chemistry
wherein
Q is selected from the group consisting of CH(alkyl), C(alkyl)2, NH, N(alkyl), O, S, SO2, Si(alkyl)2, P(O)(aryl), P(O)(alkyl), PO2H, PO2(alkyl), Se, and replaced with two H atoms;
L is independently selected from the group consisting of O, OH, NH2, NH(alkyl), NH(deuterated alkyl), N(alkyl)2, N(deuterated alkyl)2, NH(aryl), N(aryl)2, N(alkyl)(aryl), N(deuterated alkyl) (aryl), substituted or unsubstituted cyclic amines with a ring size of 3, 4, 5, 6, 7, 8, or 9 atoms, and substituted or unsubstituted deuterated cyclic amines with a ring size of 3, 4, 5, 6, 7, 8, or 9 atoms, so long as when Q is O then L is not O or OH;
R1, R2, R3, and R4 are independently selected from the group consisting of H, D, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), N3, NH2, NH(alkyl), N(alkyl)2, NH(aryl), N(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H, alkyl and substituted alkyl, aryl and substituted aryl, alkenyl and substituted alkenyl, alkynyl or substituted alkynyl, or where each adjacent R substituent and L substituent, taken together with the carbon atoms to which they are bonded, independently form a substituted or unsubstituted ring containing 3, 4, 5, 6, 7, 8, or 9 atoms;
X is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, CN, COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)N(alkyl)2, C(O)NH(aryl), and C(O)N(aryl)2;
when W is not present in the structure, Z is selected from the group consisting of H, halogen, OH, O(alkyl), O(aryl), COO, COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)N(alkyl)2, C(O)NH(aryl), C(O)N(aryl)2, PO3H2, SO3H, alkyl, substituted alkyl, alkenyl, and substituted alkenyl; and
when W is present in the structure, Z is selected from the group consisting of C(O), SO2, PO2H, or CR2 where each R is independently selected from the group consisting of H, alkyl, and substituted alkyl; and W is selected from the group consisting of O, S, C(O), C(N2), NH, N(alkyl), N(aryl), N(SO2R) where R can be alkyl, substituted alkyl, or CN.