2-((2-bromoethyl)amino)-N-(2-methoxyphenyl)-6-((4-nitrophenyl)thio)benzamide

ID: ALA4083651

PubChem CID: 118387073

Max Phase: Preclinical

Molecular Formula: C22H20BrN3O4S

Molecular Weight: 502.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1NC(=O)c1c(NCCBr)cccc1Sc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C22H20BrN3O4S/c1-30-19-7-3-2-5-17(19)25-22(27)21-18(24-14-13-23)6-4-8-20(21)31-16-11-9-15(10-12-16)26(28)29/h2-12,24H,13-14H2,1H3,(H,25,27)

Standard InChI Key:  DKAUKVNWGYUJBM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    9.0923   -8.3535    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0954   -6.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3803   -7.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3807   -7.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739   -8.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -7.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9664   -7.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6732   -6.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8025   -7.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0950   -5.8824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0840   -9.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7953   -9.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7957  -10.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0847  -10.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3817  -10.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3814   -9.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0851  -11.6353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7964  -12.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3783  -12.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8018   -5.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8015   -4.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5042   -4.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2154   -4.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2158   -5.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5049   -5.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0861   -4.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3676   -4.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6732   -5.8904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9655   -5.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9655   -4.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2578   -4.2560    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  2  9  2  0
  2 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 17 18  2  0
 17 19  1  0
 14 17  1  0
  1 11  1  0
  4  1  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 26 27  1  0
 21 26  1  0
 10 20  1  0
  8 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4083651

   2-(2-bromoethylamino)-N-(2-methoxyphenyl)-6-(4-nitrophenyl)sulfanyl-benzamide

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: 502.39

Molecular Weight (Monoisotopic): 501.0358

AlogP: 5.81

#Rotatable Bonds: 9

Polar Surface Area: 93.50

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 1.94

CX LogP: 6.01

CX LogD: 6.01

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.22

Np Likeness Score: -1.47

References

1. Zhou M, Luo RH, Hou XY, Wang RR, Yan GY, Chen H, Zhang RH, Shi JY, Zheng YT, Li R, Wei YQ..  (2017)  Synthesis, biological evaluation and molecular docking study of N-(2-methoxyphenyl)-6-((4-nitrophenyl)sulfonyl)benzamide derivatives as potent HIV-1 Vif antagonists.,  129  [PMID:28235704] [10.1016/j.ejmech.2017.01.010]

Source

Source(1):

• Scientific Literature