(R)-7-[3-(1-amino-1-methyl-ethyl)-pyrrolidin-1-yl]-9-cyclopropyl-6-fluoro-8-methoxy-9H isothiazolo[5,4-b]quinoline-3,4-dione

ID: ALA1256993

Cas Number: 922491-46-1

PubChem CID: 16048804

Max Phase: Preclinical

Molecular Formula: C21H25FN4O3S

Molecular Weight: 432.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ACH-702 | ACH-702|922491-46-1|UNII-35QF8GE1L1|35QF8GE1L1|ACH702|ACH 702|Isothiazolo(5,4-b)quinoline-3,4(2H,9H)-dione, 7-((3R)-3-(1-amino-1-methylethyl)-1-pyrrolidinyl)-9-cyclopropyl-6-fluoro-8-methoxy-|CHEMBL1256993|(r)-7-(3-(2-aminopropan-2-yl)pyrrolidin-1-yl)-9-cyclopropyl-6-fluoro-8-methoxyisothiazolo[5,4-b]quinoline-3,4(2h,9h)-dione|SCHEMBL728226|BDBM50330327|AKOS040745465|Q27256483|(R)-7-[3-(1-amino-1-methyl-ethyl)-pyrrolidin-1-yl]-9-cyclopropyl-6-fluoro-8-methoxy-9H isothiazolo[5,4-b]quinoShow More⌵

Canonical SMILES:  COc1c(N2CC[C@@H](C(C)(C)N)C2)c(F)cc2c(=O)c3c(=O)[nH]sc3n(C3CC3)c12

Standard InChI:  InChI=1S/C21H25FN4O3S/c1-21(2,23)10-6-7-25(9-10)16-13(22)8-12-15(18(16)29-3)26(11-4-5-11)20-14(17(12)27)19(28)24-30-20/h8,10-11H,4-7,9,23H2,1-3H3,(H,24,28)/t10-/m1/s1

Standard InChI Key:  CECJUHKZSOSOJJ-SNVBAGLBSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
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   -1.1649    0.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4520    1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621    0.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750    0.0622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773    1.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9773    2.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9727   -0.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595   -1.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844   -1.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6946    1.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6954    0.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813    0.2210    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    0.8897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800    1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7341    2.3422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8782    1.7121    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8796    0.0607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6344    0.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868   -0.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7749   -0.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680   -0.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -0.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -0.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620   -1.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0119    0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8076    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4243   -0.8416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
  1  2  2  0
  5  8  1  0
  6  7  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  7 14  1  0
 17 18  2  0
 13  8  1  0
  1 19  1  0
  5  4  2  0
  2 20  1  0
 20 21  1  0
  8  9  2  0
  4  1  1  0
  7 10  1  0
 11 10  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 12 11  1  0
 22 25  1  1
 10 12  1  0
  3 26  1  0
  5  6  1  0
 26 27  1  0
 25 28  1  0
 13 14  2  0
 25 29  1  0
  2  3  1  0
 25 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1256993

   Isothiazolo(5,4-b)quinoline-3,4(2H,9H)-dione, 7-((3R)-3-(1-amino-1-methylethyl)-1-pyrrolidinyl)-9-cyclopropyl-6-fluoro-8-methoxy-

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

Calculated Properties

Molecular Weight: 432.52

Molecular Weight (Monoisotopic): 432.1631

AlogP: 2.95

#Rotatable Bonds: 4

Polar Surface Area: 93.35

Molecular Species: ZWITTERION

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.81

CX Basic pKa: 10.11

CX LogP: 1.15

CX LogD: 1.16

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: -0.21

References

1. Vera-Cabrera L, Campos-Rivera MP, Escalante-Fuentes WG, Pucci MJ, Ocampo-Candiani J, Welsh O..  (2010)  In vitro activity of ACH-702, a new isothiazoloquinolone, against Nocardia brasiliensis compared with econazole and the carbapenems imipenem and meropenem alone or in combination with clavulanic acid.,  54  (5): [PMID:20308390] [10.1128/aac.01520-09]

2. Molina-Torres CA, Ocampo-Candiani J, Rendón A, Pucci MJ, Vera-Cabrera L..  (2010)  In vitro activity of a new isothiazoloquinolone, ACH-702, against Mycobacterium tuberculosis and other mycobacteria.,  54  (5): [PMID:20231398] [10.1128/aac.01603-09]

3. Pucci MJ, Ackerman M, Thanassi JA, Shoen CM, Cynamon MH..  (2010)  In vitro antituberculosis activities of ACH-702, a novel isothiazoloquinolone, against quinolone-susceptible and quinolone-resistant isolates.,  54  (8): [PMID:20516287] [10.1128/aac.00287-10]

4. Kim HY, Wiles JA, Wang Q, Pais GC, Lucien E, Hashimoto A, Nelson DM, Thanassi JA, Podos SD, Deshpande M, Pucci MJ, Bradbury BJ..  (2011)  Exploration of the activity of 7-pyrrolidino-8-methoxyisothiazoloquinolones against methicillin-resistant Staphylococcus aureus (MRSA).,  54  (9): [PMID:21425851] [10.1021/jm101604v]

Source

Source(1):

• Scientific Literature