ID: ALA15549

Max Phase: Preclinical

Molecular Formula: C17H17F2N3O3

Molecular Weight: 349.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)c1cn(C2CC2)c2c(F)c(N3CCNCC3)c(F)cc2c1=O

Standard InChI:  InChI=1S/C17H17F2N3O3/c18-12-7-10-14(13(19)15(12)21-5-3-20-4-6-21)22(9-1-2-9)8-11(16(10)23)17(24)25/h7-9,20H,1-6H2,(H,24,25)

Standard InChI Key:  CZXWNPNFWRABAP-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 349.34

Molecular Weight (Monoisotopic): 349.1238

AlogP: 1.72

#Rotatable Bonds: 3

Polar Surface Area: 74.57

Molecular Species: ZWITTERION

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 5.46

CX Basic pKa: 8.61

CX LogP: -0.71

CX LogD: -0.72

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: -0.57

References

1. Domagala JM, Bridges AJ, Culbertson TP, Gambino L, Hagen SE, Karrick G, Porter K, Sanchez JP, Sesnie JA, Spense FG..  (1991)  Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship.,  34  (3): [PMID:1848296] [10.1021/jm00107a039]

2. Hagen SE, Domagala JM, Heifetz CL, Johnson J..  (1991)  Synthesis and biological activity of 5-alkyl-1,7,8-trisubstituted-6-fluoroquinoline-3-carboxylic acids.,  34  (3): [PMID:2002456] [10.1021/jm00107a040]

3. Araki K, Kuroda T, Uemori S, Moriguchi A, Ikeda Y, Hirayama F, Yokoyama Y, Iwao E, Yakushiji T..  (1993)  Quinolone antimicrobial agents substituted with morpholines at the 7-position. Syntheses and structure-activity relationships.,  36  (10): [PMID:8388467] [10.1021/jm00062a007]

4. Miyamoto T, Matsumoto J, Chiba K, Egawa H, Shibamori K, Minamida A, Nishimura Y, Okada H, Kataoka M, Fujita M..  (1990)  Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency.,  33  (6): [PMID:2342057] [10.1021/jm00168a018]

5. Dax S, Pruess D, Rossman P, Wei C.  (1993)  Synthesis and mechanistic studies of a tetrazole-tethered cephalosporin-quinolone hybrid,  3  (2): [10.1016/S0960-894X(01)80878-7]

6. Uno T, Okuno T, Kawakami K, Sakamoto F, Tsukamoto G..  (1993)  Synthesis of antimicrobial agents. 5. In vivo metabolism of 7-(4-hydroxypiperazin-1-yl)quinolones.,  36  (19): [PMID:8410985] [10.1021/jm00071a001]

7. Sanchez JP, Bridges AJ, Bucsh R, Domagala JM, Gogliotti RD, Hagen SE, Heifetz CL, Joannides ET, Sesnie JC, Shapiro MA..  (1992)  New 8-(trifluoromethyl)-substituted quinolones. The benefits of the 8-fluoro group with reduced phototoxic risk.,  35  (2): [PMID:1732554] [10.1021/jm00080a023]

8. Zhang Z, Zhou W, Yu A..  (2004)  Synthesis and antibacterial activity of 7-(substituted)aminomethyl quinolones.,  14  (2): [PMID:14698166] [10.1016/j.bmcl.2003.10.059]

9. Suto MJ, Domagala JM, Roland GE, Mailloux GB, Cohen MA..  (1992)  Fluoroquinolones: relationships between structural variations, mammalian cell cytotoxicity, and antimicrobial activity.,  35  (25): [PMID:1469702] [10.1021/jm00103a013]

10. Domagala JM, Hagen SE, Heifetz CL, Hutt MP, Mich TF, Sanchez JP, Trehan AK..  (1988)  7-substituted 5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3- quinolinecarboxylic acids: synthesis and biological activity of a new class of quinolone antibacterials.,  31  (3): [PMID:3346869] [10.1021/jm00398a003]

11. Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Remuzon P, Weber A, Oki T, Masuyoshi M..  (1989)  Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationships of new 1-substituted derivatives.,  32  (3): [PMID:2918499] [10.1021/jm00123a005]

12. Kiely JS, Hutt MP, Culbertson TP, Bucsh RA, Worth DF, Lesheski LE, Gogliotti RD, Sesnie JC, Solomon M, Mich TF..  (1991)  Quinolone antibacterials: preparation and activity of bridged bicyclic analogues of the C7-piperazine.,  34  (2): [PMID:1995890] [10.1021/jm00106a029]

13. Sanchez JP, Domagala JM, Hagen SE, Heifetz CL, Hutt MP, Nichols JB, Trehan AK..  (1988)  Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids.,  31  (5): [PMID:3361584] [10.1021/jm00400a016]

Source

Source(1):

• Scientific Literature