Analogs of 4-bromo-2,5-dimethoxyphenethylamine

A compound of Formula (I):

• or an isotopologue, or a pharmaceutically acceptable salt thereof, wherein:
• R1 is selected from hydrogen, Ra, Rb and Ra substituted with one or more Rb;
• Ra is, for each occurrence, independently selected from the group consisting of C1-6 alkyl, C2-C6 alkenyl, C1-6 haloalkyl, C3-6 cycloalkyl, C3-6 heteroalkyl;
• Rb is selected from the group consisting of, cyano (—CN), halogen, nitro (—NO2), —NRcRc, —N(H)C(O)Ra, —C(═O)Ra, —ORa, —SRa, —SeRa, S(═O)Rd, —S(═O)2Rd, —Si(Ra)3, and —SF5;
• Rc is, for each occurrence, independently selected from hydrogen, C1-6 alkyl, and C3-6 cycloalkyl, or two Rc, together with the nitrogen atom to which they are attached, form a heterocycloalkyl optionally substituted with one or two Rb;
• Rd is selected from the group consisting of C1-6 alkyl, C1-6 haloalkyl, C3-6 cycloalkyl, aryl, heteroaryl, and —NRcRc;
• Re is, for each occurrence, hydrogen, C1-6 alkyl, —C(═O)OR3, or —CH2NHC(═O)R4;
• R2 is —C(═O)OR3, —C(═O)R4, —CH(R5)OR6, —C(═O)OCH(R5)OC(═O)R6, —C(═O)OCH(R5)OC(═O)OR6, —C(═O)OCH(R5)OC(═O)NHR6, —CH(R5)C(═O)R6, —C(═O)CH(R5)N(R9)C(O)R6, —CH(R5)NHC(O)R6, —S(═O)2R7, —S(═O)2OR7, —P(O)OR5[N(R9)R10], —C(═O)N(R9)R10, —P(═O)OR11(OR12), —CH(R4)OP(═O)OR8[N(R9)R10], or —CH(R4)OP(═O)OR11(OR12);
• or R2 and Re on the same N atom are taken together with the N to which they are attached to form a succinimide, maleimide, or phthalimide, wherein the succinimide, maleimide, or phthalimide is unsubstituted or substituted with one or more RA;
• each of R3, R4, R6, R7, and R8 is independently alkyl, alkenyl, haloalkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, wherein alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is unsubstituted or substituted with one or more RA;
• R5 is hydrogen, alkyl, alkenyl, haloalkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, wherein alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is unsubstituted or substituted with one or more RA;
• each of R9 and R10 is independently hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, wherein alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is unsubstituted or substituted with one or more RA, or R9 and R10 together with the atom to which they are attached form a heterocycloalkyl ring or a heteroaryl ring that is unsubstituted or substituted with one or more RA;
• each of R11 and R12 is independently hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, wherein alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is unsubstituted or substituted with one or more RA, or R11 and R12 together with the atoms to which they are attached form a heterocycloalkyl ring that is unsubstituted or substituted with one or more RA;
• each RA is independently alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, an amino acid side chain, —OR13, —N(R18)R19, —C(═O)OR13, —N(R13)C(═O)OR14, —N(R13)C(═O)R14, —C(═O)R14, —OC(═O)R15, —OC(═O)OR16, —OP(═O)OR17[N(R18)R19], —C(═O)N(R18)R19, —OC(═O)N(R18)R19, or —OP(═O)OR20(OR21), wherein alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is unsubstituted or substituted with alkyl, aryl, halogen, —OR13, —NR(R18)R19, —C(═O)R14, —OC(═O)R15, —OC(═O)OR16, —OC(═O)N(R18)R19, or —OP(O)OR20(OR21);
• each of R13, R14, R15, R16, or R17 is independently hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, wherein alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is unsubstituted or substituted with one or more RB;
• each of R18 and R19 is independently hydrogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, wherein alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is unsubstituted or substituted with one or more RB;
• or R18 and R19 together with the atom to which they are attached form a heterocycloalkyl ring or heteroaryl ring, each of which is unsubstituted or substituted with one or more RB;
• each of R20 and R21 is independently hydrogen, alkyl, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, wherein alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is unsubstituted or substituted with one or more RB, or R20 and R21 together with the atoms to which they are attached form a heterocycloalkyl ring that is unsubstituted or substituted with one or more RB;
• and
• each RB is independently halogen, amino, cyano, hydroxyl, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, —C(═O)CH3, —C(═O)Ph, or heteroarylalkyl, wherein cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is unsubstituted or substituted with one or more halogen, amino, cyano, hydroxyl, alkyl, acetyl, or benzoyl.