# US 2015/0148314 A1 · Seriniquinones, melanoma-specific anticancer agents

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- Number: US 2015/0148314 A1
- Document ID: US20150148314A1
- Status: Published application
- Kind: A1
- Application number: 14/606,938
- Filed: 2015-01-27
- Published: 2015-05-28
- Earliest claimed: 2012-07-27
- Assignees: The Regents of the University of California, a California corporation
- Applicants: The Regents of the University of California, a California corporation
- Inventors: William Fenical; Paul R. Jensen; James J. La Clair; Lynnie Trzoss; Takashi Fukuda
- Web page: https://patentgrep.com/patent/US20150148314A1

## CPC

- C07D 333/74: Naphthothiophenes
- A61P 35/00: Antineoplastic agents
- C07D 209/56: Ring systems containing three or more rings
- C07D 209/80: [b, c]- or [b, d]-condensed
- C07D 307/77: ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D 307/92: Naphthofurans; Hydrogenated naphthofurans
- C07D 333/50: condensed with carbocyclic rings or ring systems
- C07D 339/08: Six-membered rings
- C07D 409/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 495/04: Ortho-condensed systems
- C07F 9/65742: {non-condensed with carbocyclic rings or heterocyclic rings or ring systems}
- G01N 33/5011: {for testing antineoplastic activity}
- A61K 31/381: having five-membered rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

There are provided, inter alia, derivatives of seriniquinone and methods useful for the treatment of cancer, and in particular treatment of melanoma and prostate cancer.

## Claims

### Claim 1

A compound having the formula:
or pharmaceutically acceptable salt thereof,
wherein
A is N or —CR4;
X is —S—, —NR21—, or —O—;
R1, R2, R3, R4, R5, R6, R7, and R8 are independently hydrogen, halogen, —N3, —NHC═(O)NHNH2, —CN, —CF3, —CCl3, —CBr3, —CI3, —NR9R10, —C(O)R11, —C(O)NR9R10, —NR12C(O)R11, —S(O)nR13, —S(O)nNR9R10, —NR12S(O)nR13, —NO2, —OR14, —SR14, —NR15, —OCOR16, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, wherein two of R1, R2, R3, R4, R5, R6, R7, and R8 are optionally joined to form a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocycloalkyl;
R9, R10 R11, R12, R13, R14, R15, and R16, are independently hydrogen, halogen, —CN, —CF3, —CCl3, —CBr3, —CI3, —OH, —NH2, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R21 is hydrogen or unsubstituted C1-C5 alkyl;
n is 1 to 4; and
wherein if X is S and A is CR4, at least one of R1, R2, R3, R4, R5, R6, R7, and R8 is not hydrogen.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1, R2, R3, R4, R5, R6, R7, and R8 are a hydrophilic moiety.

### Claim 3 (depends on 1)

The compound of claim 1, said compound having the formula:
wherein R2 is substituted or unsubstituted heteroalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

### Claim 4 (depends on 3)

The compound of claim 3, wherein said heteroalkyl is R2a-substituted heteroalkyl, wherein R2a is hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OH, —NH2, —COOH, —CONH2, —NO2, —SH, —SO2, —SO2Cl, —SO3H, —SO4H, —SO2NH2, —NHNH2, —ONH2, —NHC(O)NHNH2, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

### Claim 5 (depends on 4)

The compound of claim 4, wherein said R2a-substituted heteroalkyl is —(CH2)2C(O)—R2a.

### Claim 6 (depends on 1)

The compound of claim 1, said compound having the formula:

### Claim 7 (depends on 1)

The compound of claim 1, said compound having the formula:

### Claim 8

A compound having the formula:
or pharmaceutically acceptable salt thereof,
wherein
X is —S—, —NR21—, or —O—;
R1, R2, R3, R4, R5, R6, R7, and R8 are independently hydrogen, halogen, —N3, —NHC═(O)NHNH2, —CN, —CF3, —CCl3, —CBr3, —CI3, —NR9R10, —C(O)R11, —C(O)NR9R10, —NR12C(O)R11, —S(O)nR13, —S(O)nNR9R10, —NR12S(O)nR13, —NO2, —OR14, —SR14, —NR15, —OCOR16, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, wherein two of R1, R2, R3, R4, R5, R6, R7, and R8 are optionally joined to form a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocycloalkyl;
R9, R10 R11, R12, R13, R14, R15, and R16, are independently hydrogen, halogen, —CN, —CF3, —CCl3, —CBr3, —CI3, —OH, —NH2, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R21 is hydrogen or unsubstituted C1-C5 alkyl; and
n is 1 to 4.

### Claim 9 (depends on 8)

The compound of claim 8, wherein X is —O—.

### Claim 10 (depends on 9)

The compound of claim 9, wherein R1, R2, R3, R4, R5, R6, R7, and R8 are hydrogen.

### Claim 11 (depends on 9)

The compound of claim 9, wherein R1, R2, R3, R4, R5, R6, R7, and R8 are a hydrophilic moiety.

### Claim 12

A compound having the formula:
or pharmaceutically acceptable salt thereof,
wherein
X is —S—, —NR21—, or —O—;
R1, R2, R3, R4, R5, R6, R7, and R8 are each independently hydrogen, halogen, —N3, —NHC═(O)NHNH2, —CN, —CF3, —CCl3, —CBr3, —CI3, —NR9R10, —C(O)R11, —C(O)NR9R10, —NR12C(O)R11, —S(O)nR13, —S(O)nNR9R10, —NR12S(O)nR13, —NO2, —OR14, —SR14, —NR15, —OCOR16, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, wherein two of R1, R2, R3, R4, R5, R6, R7, and R8 are optionally joined to form a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocycloalkyl;
R9, R10R11, R12, R13, R14, R15, and R16 are independently hydrogen, halogen, —CN, —CF3, —CCl3, —CBr3, —CI3, —OH, —NH2, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R21 is hydrogen or unsubstituted C1-C5 alkyl;
n is 1 to 4; and
R17, R18, R19, and R20 are independently hydrogen or substituted or unsubstituted alkyl.

### Claim 13 (depends on 12)

The compound of claim 12, wherein R1, R2, R3, R4, R5, R6, R7, and R8 are a hydrophilic moiety.

### Claim 14 (depends on 12)

The compound of claim 12, wherein R17, R18, R19, and R20 are identical.

### Claim 15 (depends on 14)

The compound of claim 14, wherein R17, R18, R19, and R20 are hydrogen, methyl, or acetyl.

### Claim 16 (depends on 15)

The compound of claim 15, wherein R17, R18, R19, and R20 are acetyl.

### Claim 17

A compound having the formula
or pharmaceutically acceptable salt thereof,
wherein
A is N or —CR4;
X is —S—, —NR21—, or —O—;
R1, R2, R3, R4, R5, R6, R7, and R8 are independently hydrogen, halogen, —N3, —NHC═(O)NHNH2, —CN, —CF3, —CCl3, —CBr3, —CI3, —NR9R10, —C(O)R11, —C(O)NR9R10, —NR12C(O)R11, —S(O)nR13, —S(O)nNR9R10, —NR12S(O)nR13, —NO2, —OR14, —SR14, —NR15, —OCOR16, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, wherein two of R1, R2, R3, R4, R5, R6, R7, and R8 are optionally joined to form a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted heterocycloalkyl;
R9, R10 R11, R12, R13, R14, R15, and R16, are independently hydrogen, halogen, —CN, —CF3, —CCl3, —CBr3, —CI3, —OH, —NH2, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R21 is hydrogen or unsubstituted C1-C5 alkyl;
n is 1 to 4′ and
R17, R18, R19, and R20 are independently hydrogen or substituted or unsubstituted alkyl.

### Claim 18 (depends on 17)

A method of treating cancer in a subject in need thereof, said method comprising administering to a subject a therapeutically effective amount of a compound of claim 17.

### Claim 19 (depends on 18)

The method of claim 18, wherein said cancer is melanoma or prostate cancer.

### Claim 20 (depends on 17)

A method of inhibiting a dermcidin protein, said method comprising contacting a dermcidin protein with a compound of claim 17, thereby inhibiting said dermcidin protein.