| US 7,378,530 B2 | ||
| Anti-cancer and anti-microbial 5-membered heterocyclic compounds | ||
| Venkata Rami Reddy Macherla, San Diego, Calif. (US); Benjamin Nicholson, Narberth, Pa. (US); and Kin Sing Lam, San Diego, Calif. (US) | ||
| Assigned to Nereus Pharmaceuticals, Inc., San Diego, Calif. (US) | ||
| Filed on Feb. 21, 2006, as Appl. No. 11/358,961. | ||
| Claims priority of provisional application 60/655605, filed on Feb. 22, 2005. | ||
| Prior Publication US 2006/0205799 A1, Sep. 14, 2006 | ||
| Int. Cl. C07D 277/02 (2006.01); C07D 263/04 (2006.01); C07D 233/02 (2006.01) | ||
| U.S. Cl. 548—182 [548/187; 548/225; 548/316.4; 548/324.1] | 35 Claims |
1. A compound having the structure of formula I:
 R1 is a molecular fragment having the structure of formula (II),
 Z is selected from the group consisting of O, S, and NR5;
R6 and R7 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted,
straight or branched chain variants of the following groups: C1-C24 alkyl, C2-C24 alkenyl, or C2-C24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl;
heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido;
phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;
R8 and R9 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted,
straight or branched chain variants of the following residues: C1-C24 alkyl, C2-C24 alkenyl, or C2-C24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl;
heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido;
phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; and halogenated alkyl including polyhalogenated alkyl; or are
separately absent;
R10 and R11 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted,
straight or branched chain variants of the following residues: C1-C24 alkyl, C2-C24 alkenyl, or C2-C24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl;
heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido;
phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;
or are separately absent;
R2 is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight
or branched chain variants of the following residues: C1-C24 alkyl, C2-C24 alkenyl, or C2-C24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; heteroaryl;
ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; hydroxy; alkylthio;
arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;
R3 is ═O;
R1′ is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight
or branched chain variants of the following groups: C1-C24 alkyl, C2-C24 alkenyl, or C2-C24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl;
heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido;
phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;
or are separately absent;
R2′ is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight
or branched chain variants of the following residues: C1-C24 alkyl, C2-C24 alkenyl, or C2-C24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; heteroaryl;
ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; hydroxy; alkylthio;
arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;
Y is separately selected from the group consisting of O, S, and NR5;
R4 and each R5 are separately selected from the group consisting of hydrogen; mono-substituted, poly-substituted or unsubstituted, straight
or branched chain variants of the following residues: C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-6 heteroalkyl, C2-6 aminoalkyl, C2-6 haloalkyl, C1-6 alkoxycarbonyl, and C2-6 hydroxyalkyl; C3-8 cycloalkyl; —C(O)—C5-6 aryl substituted with C1-3 alkyl or halo; C5-6 aryl; C5-6 heteroaryl; C5-6 cycloalkyl; and C5-6 heterocycloalkyl, or are separately absent;
any bond represented by a dashed and solid line represents a bond selected from the group consisting of a single bond and
a double bond;
any bond represented by a single dashed line is a single bond or is absent; and
any carbon-carbon double bond has a configuration selected from the group consisting of cis and trans.
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