# US 2016/0355487 A1 · Phenazine derivatives as antimicrobial agents

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- Number: US 2016/0355487 A1
- Document ID: US20160355487A1
- Status: Published application
- Kind: A1
- Application number: 15/107,531
- Filed: 2014-12-23
- Published: 2016-12-08
- Earliest claimed: 2013-12-24
- Assignees: University of Florida Research Foundation, Inc.
- Applicants: University of Florida Research Foundation, Inc.
- Inventors: Robert William Huigens, III; Shouguang Jin
- Web page: https://patentgrep.com/patent/US20160355487A1

## CPC

- C07D 241/46: Phenazines
- A61K 31/498: Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/04: Antibacterial agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 241/38: with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides novel phenazine derivatives, such as compounds of Formula (I) and (II), and pharmaceutically acceptable salts thereof. The compounds of the invention are expected to be antimicrobial agents and may act by a microbial warfare strategy (e.g., a reactive oxygen species (ROS)-based competition strategy). The present invention also provides pharmaceutical compositions, kits, uses, and methods that involve the compounds of the invention and may be useful in preventing or treating a microbial infection (e.g., a bacterial infection) in a subject, inhibiting the growth and/or reproduction of a microorganism (e.g., a bacterium), killing a microorganism (e.g., a bacterium), inhibiting the formation and/or growth of a biofilm, or reducing or clearing a biofilm.

## Claims

### Claim 1

A compound of Formula (I):
and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrugs thereof, wherein:
each instance of X is independently a halogen;
L is —OC(═O)O—, —OC(═O)—, —C(═O)O—, —NRLC(═O)—, —C(═O)NRL—, —OC(═O)NRL—, —NRLC(═O)O—, —NRLC(═O)NRL—, —OS(═O)2—, —S(═O)2O—, —NRLS(═O)2—,—S(═O)2NRL—, or —NRLS(═O)2NRL—;
each instance of RL is independently hydrogen, substituted or unsubstituted alkyl, or a nitrogen protecting group;
RA is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, or an oxygen protecting group when attached to an oxygen atom;
RB is hydrogen, halogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORB1, —N(RB1)2, —SRB1, —CN, —SCN, —C(═NRB1)RB1, —C(═NRB1)ORB1, —C(═NRB1)N(RB1)2, —C(═O)RB1, —C(═O)ORB1, —C(═O)N(RB1)2, —NO2, —NRB1C(═O)RB1, —NRB1C(═O)ORB1, —NRB1C(═O)N(RB1)2, —OC(═O)RB1, —OC(═O)ORB1, or —OC(═O)N(RB1)2;
each instance of RB1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of RB1 are joined to form a substituted or unsubstituted heterocyclic ring;
each instance of RC is independently hydrogen, halogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORC1, —N(RC1)2, —SRC1, —CN, —SCN, —C(═NRC1)RC1, —C(═NRC1)ORC1, —C(═NRC1)N(RC1)2, —C(═O)RC1, —C(═O)ORC1, —C(═O)N(RC1)2, —NO2, —NRC1C(═O)RC1, —NRC1C(═O)ORC1, —NRC1C(═O)N(RC1)2, —OC(═O)RC1, —OC(═O)ORC1, or —OC(═O)N(RC1)2, or two instances of RC are joined to form a substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl ring;
each instance of RC1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of RC1 are joined to form a substituted or unsubstituted heterocyclic ring; and
n is 0, 1, 2, 3, or 4.

### Claim 2

A compound of Formula (II):
and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrugs thereof, wherein:
each instance of X is independently a halogen;
LRA is a linker selected from the group consisting of substituted and unsubstituted alkylene, substituted and unsubstituted alkenylene, substituted and unsubstituted alkynylene, substituted and unsubstituted heteroalkylene, substituted and unsubstituted heteroalkenylene, substituted and unsubstituted heteroalkynylene, substituted and unsubstituted heterocyclylene, substituted and unsubstituted carbocyclylene, substituted and unsubstituted arylene, substituted and unsubstituted heteroarylene, and combinations thereof;
L is —OC(═O)O—, —OC(═O)—, —C(═O)O—, —NRLC(═O)—, —C(═O)NRL—, —OC(═O)NRL—, —NRLC(═O)O—, —NRLC(═O)NRL—, —OS(═O)2—, —S(═O)2O—, —NRLS(═O)2—,—S(═O)2NRL—, or —NRLS(═O)2NRL—;
each instance of RL is independently hydrogen, substituted or unsubstituted alkyl, or a nitrogen protecting group;
RB is hydrogen, halogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORB1,—N(RB1)2, —SRB1, —CN, —SCN, —C(═NRB1)RB1, —C(═NRB)ORB1, —C(═NRB1)N(RB1)2, —C(═O)RB1, —C(═O)ORB1, —C(═O)N(RB1)2, —NO2, —NRB1C(═O)RB1, —NRB1C(═O)ORB1, —NRB1C(═O)N(RB1)2, —OC(═O)RB1, —OC(═O)ORB1, or —OC(═O)N(RB1)2;
each instance of RB1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of RB1 are joined to form a substituted or unsubstituted heterocyclic ring;
each instance of RC is independently hydrogen, halogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORC1, —N(RC1)2, —SRC1, —CN, —SCN, —C(═NRC1)RC1, —C(═NRC1)ORC1, —C(═NRC1)N(RC1)2, —C(═O)RC1, —C(═O)ORC1, —C(═O)N(RC1)2, —NO2, —NRC1C(═O)RC1, —NRC1C(═O)ORC1, —NRC1C(═O)N(RC1)2, —OC(═O)RC1, —OC(═O)ORC1, or —OC(═O)N(RC1)2, or two instances of RC are joined to form a substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl ring;
each instance of RC1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of RC1 are joined to form a substituted or unsubstituted heterocyclic ring; and
n is 0, 1, 2, 3, or 4.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 13 (depends on 1)

The compound of claim 1, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 14 (depends on 2)

The compound of claim 2, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 15 (depends on 1, 2)

The compound of any one of claims 1, 2, and 5-7, wherein at least one instance of RL is hydrogen.

### Claim 16 (depends on 1, 2)

The compound of any one of claims 1, 2, and 5-7, wherein at least one instance of RL is unsubstituted C1-6 alkyl or C1-6 alkyl substituted with at least one halogen.

### Claim 17 (depends on 1, 2)

The compound of any one of claims 1, 2, and 3-13, wherein RA is substituted or unsubstituted alkyl.

### Claim 18 (depends on 17)

The compound of claim 17, wherein RA is unsubstituted C1-6 alkyl.

### Claim 19 (depends on 17)

The compound of claim 17, wherein RA is C1-6 alkyl substituted with at least one halogen.

### Claim 20 (depends on 17)

The compound of claim 17, wherein RA is —CH3, —CF3, —CCl3, —CH2CCl3, —C2H5, —(CH2)2CH3, or —CH(CH3)2.

### Claim 21 (depends on 1, 2)

The compound of any one of claims 1, 2, and 3-13, wherein RA is substituted or unsubstituted alkenyl.

### Claim 22 (depends on 21)

The compound of claim 21, wherein RA is substituted or unsubstituted styryl.

### Claim 23 (depends on 1, 2)

The compound of any one of claims 1, 2, and 3-13, wherein RA is substituted or unsubstituted alkoxyalkyl.

### Claim 24 (depends on 1, 2)

The compound of any one of claims 1, 2, and 3-13, wherein RA is substituted or unsubstituted, 6- to 14-membered aryl.

### Claim 25 (depends on 24)

The compound of claim 24, wherein RA is substituted phenyl.

### Claim 26 (depends on 24)

The compound of claim 24, wherein RA is phenyl substituted with one, two, three, four, or five substituents independently selected from the group consisting of halogen, unsubstituted C1-6 alkyl, C1-6 alkyl substituted with at least one halogen, and —ORA1, wherein RA1 is unsubstituted C1-6 alkyl, C1-6 alkyl substituted with at least one halogen, or an oxygen protecting group.

### Claim 27 (depends on 24)

The compound of claim 24, wherein RA is of the formula:

### Claim 28 (depends on 24)

The compound of claim 24, wherein RA is unsubstituted phenyl.

### Claim 29 (depends on 1, 2)

The compound of any one of claims 1, 2, and 3-13, RA is substituted or unsubstituted aryl fused with a substituted or unsubstituted 5- or 6-membered heterocyclic ring.

### Claim 30 (depends on 29)

The compound of claim 29, wherein RA is of the formula:

### Claim 31 (depends on 1, 2)

The compound of any one of claims 1, 2, and 3-13, wherein RA is substituted or unsubstituted heteroaryl.

### Claim 32 (depends on 31)

The compound claim 31, wherein RA is substituted or unsubstituted 5-membered, monocyclic heteroaryl.

### Claim 33 (depends on 32)

The compound of claim 32, wherein RA is substituted or unsubstituted furan or thiophene.

### Claim 34 (depends on 1, 2, 3, 4, 5, 6, 7, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33)

The compound of any one of claims 1-7 and 13-33, wherein RB is hydrogen.

### Claim 35 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34)

The compound of any one of claims 1-11 and 13-34, wherein all instances of RC are hydrogen.

### Claim 36 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34)

The compound of any one of claims 1-11 and 13-34, wherein at least one instance of RC is halogen, substituted or unsubstituted alkyl, —ORC1, or —CN.

### Claim 37 (depends on 1, 2)

The compound of any of any one of claims 1, 2, and 14-36 wherein at least one instance of X is —Cl, —Br, or —I.

### Claim 38 (depends on 2, 14, 15, 16)

The compound of any of any one of claims 2, 14-16, and 34-37, wherein LRA is substituted or unsubstituted alkylene or substituted or unsubstituted heteroalkylene.

### Claim 39 (depends on 38)

The compound of claim 38, wherein LRA is substituted or unsubstituted C1-6alkylene or substituted or unsubstituted heteroC1-6alkylene.

### Claim 40 (depends on 39)

The compound of claim 39, wherein LRA is unsubstituted C1-6alkylene.

### Claim 41 (depends on 1, 2)

The compound of any one of claims 1 and 2, wherein the compound is of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 42 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41)

A pharmaceutical composition comprising a compound of any one of claims 1-41, or a pharmaceutically acceptable salt thereof, and optionally a pharmaceutically acceptable excipient.

### Claim 43 (depends on 42)

The pharmaceutical composition of claim 42 further comprising an additional pharmaceutical agent.

### Claim 44 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)

A method of preventing or treating a microbial infection in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound of any one of claims 1-41, or a pharmaceutical acceptable salt thereof, or a pharmaceutical composition of claim 42 or 43.

### Claim 45 (depends on 44)

The method of claim 44, wherein the subject is a human.

### Claim 46 (depends on 44)

The method of claim 44, wherein the subject is a non-human animal.

### Claim 47 (depends on 44, 45, 46)

The method of any one of claims 44-46, wherein the microbial infection is caused by a multidrug-resistant microorganism.

### Claim 48 (depends on 44, 45, 46, 47)

The method of any one of claims 44-47, wherein the microbial infection is associated with a biofilm.

### Claim 49 (depends on 44, 45, 46, 47, 48)

The method of any one of claims 44-48, wherein the microbial infection is a microbial respiratory tract infection, a microbial gastrointestinal tract infection, a microbial urogenital tract infection, a microbial bloodstream infection, a microbial ear infection, a microbial skin infection, a microbial oral infection, a microbial dental infection, a microbial wound or surgical site infection, a microbial infection associated with cystic fibrosis, or a microbial infection associated with an implanted device.

### Claim 50 (depends on 44, 45, 46, 47, 48)

The method of any one of claims 44-48, wherein the microbial infection is microbial pneumonia, microbial sinusitis, microbial endocarditis, gingivitis, dental plaque, a microbial infection associated with a dental implant, a microbial infection associated with a catheter, a microbial infection associated with a heart valve, a microbial infection associated with an intrauterine device, or a microbial infection associated with a joint prosthesis.

### Claim 51 (depends on 44, 45, 46, 47, 48, 49, 50)

The method of any one of claims 44-50, wherein the microbial infection is a bacterial infection.

### Claim 52 (depends on 51)

The method of claim 51, wherein the bacterial infection is caused by a Gram-positive bacterium.

### Claim 53 (depends on 51)

The method of claim 51, wherein the bacterial infection is caused by a Gram-negative bacterium.

### Claim 54 (depends on 51)

The method any one of claim 51, wherein the bacterial infection is a methicillin-resistant Staphylococcus aureus (MRSA)-related infection.

### Claim 55 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)

A method of inhibiting the growth of a microorganism, the method comprising contacting the microorganism with an effective amount of a compound of any one of claims 1-41, or a pharmaceutical acceptable salt thereof, or a pharmaceutical composition of claim 42 or 43.

### Claim 56 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)

A method of inhibiting the reproduction of a microorganism, the method comprising contacting the microorganism with an effective amount of a compound of any one of claims 1-41, or a pharmaceutical acceptable salt thereof, or a pharmaceutical composition of claim 42 or 43.

### Claim 57 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)

A method of killing a microorganism, the method comprising contacting the microorganism with an effective amount of a compound of any one of claims 1-41, or a pharmaceutical acceptable salt thereof, or a pharmaceutical composition of claim 42 or 43.

### Claim 58 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)

A method of inhibiting the formation of a biofilm, the method comprising contacting the biofilm with an effective amount of a compound of any one of claims 1-41, or a pharmaceutical acceptable salt thereof, or a pharmaceutical composition of claim 42 or 43.

### Claim 59 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)

A method of inhibiting the growth of a biofilm, the method comprising contacting the biofilm with an effective amount of a compound of any one of claims 1-41, or a pharmaceutical acceptable salt thereof, or a pharmaceutical composition of claim 42 or 43.

### Claim 60 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)

A method of reducing or clearing a biofilm, the method comprising contacting the biofilm with an effective amount of a compound of any one of claims 1-41, or a pharmaceutical acceptable salt thereof, or a pharmaceutical composition of claim 42 or 43.

### Claim 61 (depends on 48, 58, 59, 60)

The method of any one of claims 48 and 58-60, wherein the biofilm comprises a microorganism.

### Claim 62 (depends on 47, 55, 56, 57)

The method of any one of claims 47, 55-57, and 61, wherein the microorganism is present in vitro.

### Claim 63 (depends on 47, 55, 56, 57)

The method of any one of claims 47, 55-57, and 61, wherein the microorganism is present in vivo.

### Claim 64 (depends on 47, 55, 56, 57)

The method of any one of claims 47, 55-57, and 61-63, wherein the microorganism is a multidrug-resistant microorganism.

### Claim 65 (depends on 47, 55, 56, 57)

The method of any one of claims 47, 55-57, and 61-64, wherein the microorganism is a bacterium.

### Claim 66 (depends on 65)

The method of claim 65, wherein the bacterium is a Gram-positive bacterium.

### Claim 67 (depends on 65)

The method of claim 65, wherein the bacterium is a Staphylococcus species.

### Claim 68 (depends on 65)

The method of claim 65, wherein the bacterium is a Staphylococcus aureus or Staphylococcus epidermidis strain.

### Claim 69 (depends on 65)

The method of claim 65, wherein the bacterium is methicillin-resistant Staphylococcus aureus (MRSA).

### Claim 70 (depends on 65)

The method of claim 65, wherein the bacterium is a Streptococcus, Enterococcus, Listeria, or Clostridium species.

### Claim 71 (depends on 65)

The method of claim 65, wherein the bacterium is a Gram-negative bacterium.

### Claim 72 (depends on 65)

The method of claim 65, wherein the bacterium is an Acinetobacter species.

### Claim 73 (depends on 65)

The method of claim 65, wherein the bacterium is an Acinetobacter baumannii strain.

### Claim 74 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)

A kit comprising:
a compound of any one of claims 1-41, or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition of claim 42 or 43; and
instructions for using the kits.