(R)-5'-Chloro-3-((S)-1-(4-chlorophenyl)ethyl)-1'-ethyl-4,6-dihydrospiro[[1,2,3]triazolo[4,5-b]pyridine-7,3'-indoline]-2',5(3H)-dione

ID: ALA4483405

PubChem CID: 155540735

Max Phase: Preclinical

Molecular Formula: C22H19Cl2N5O2

Molecular Weight: 456.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1C(=O)[C@]2(CC(=O)Nc3c2nnn3[C@@H](C)c2ccc(Cl)cc2)c2cc(Cl)ccc21

Standard InChI:  InChI=1S/C22H19Cl2N5O2/c1-3-28-17-9-8-15(24)10-16(17)22(21(28)31)11-18(30)25-20-19(22)26-27-29(20)12(2)13-4-6-14(23)7-5-13/h4-10,12H,3,11H2,1-2H3,(H,25,30)/t12-,22+/m0/s1

Standard InChI Key:  JVDCXWMZHGRZAJ-AMXDTQDGSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   19.8680   -6.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6668   -7.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6656   -7.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3778   -8.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3760   -6.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0888   -7.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0935   -7.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8777   -8.2448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3551   -7.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1586   -5.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1586   -6.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8680   -5.2663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5774   -5.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5819   -6.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3612   -6.7482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8359   -6.0832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3540   -5.4235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1764   -7.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4456   -5.2725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9548   -6.7647    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.0559   -5.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0492   -4.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7711   -5.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7607   -3.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7543   -2.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0386   -2.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3319   -2.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3418   -3.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0308   -1.7284    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.8726   -9.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5777   -9.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  1  9  1  1
  1  6  1  0
 10 11  1  0
 10 12  1  0
 11  1  1  0
  1 14  1  0
 13 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
  9 18  2  0
 10 19  2  0
  2 20  1  0
 17 21  1  0
 21 22  1  0
 21 23  1  6
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
 26 29  1  0
  8 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483405

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.33

Molecular Weight (Monoisotopic): 455.0916

AlogP: 4.19

#Rotatable Bonds: 3

Polar Surface Area: 80.12

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.06

CX Basic pKa: ┄

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.64

Np Likeness Score: -1.07

References

1. Xu J, Xie X, Ye N, Zou J, Chen H, White MA, Shi PY, Zhou J..  (2019)  Design, Synthesis, and Biological Evaluation of Substituted 4,6-Dihydrospiro[[1,2,3]triazolo[4,5-b]pyridine-7,3'-indoline]-2',5(3H)-dione Analogues as Potent NS4B Inhibitors for the Treatment of Dengue Virus Infection.,  62  (17): [PMID:31403780] [10.1021/acs.jmedchem.9b00698]

Source

Source(1):

• Scientific Literature