4-fluoro-3-[(4-hydroxy-1-piperidyl)sulfonyl]-N-(3,4,5-trifluorophenyl)benzamide

ID: ALA4533071

Cas Number: 1445790-55-5

PubChem CID: 89663273

Product Number: N413621, Order Now?

Max Phase: Preclinical

Molecular Formula: C18H16F4N2O4S

Molecular Weight: 432.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(F)c(F)c(F)c1)c1ccc(F)c(S(=O)(=O)N2CCC(O)CC2)c1

Standard InChI:  InChI=1S/C18H16F4N2O4S/c19-13-2-1-10(18(26)23-11-8-14(20)17(22)15(21)9-11)7-16(13)29(27,28)24-5-3-12(25)4-6-24/h1-2,7-9,12,25H,3-6H2,(H,23,26)

Standard InChI Key:  KKMFSVNFPUPGCA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    7.3300  -18.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5128  -18.1350    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9214  -18.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743  -13.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732  -14.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6812  -14.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3909  -14.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3880  -13.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6794  -13.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992  -14.8753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1005  -15.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8089  -16.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934  -16.1022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8055  -16.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5131  -17.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2211  -16.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2172  -16.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5091  -15.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665  -13.2403    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9300  -17.3186    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8067  -18.5484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0962  -18.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922  -18.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3930  -19.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1039  -19.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140  -19.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862  -19.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651  -14.8763    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6770  -12.4227    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 12  1  0
  4 19  1  0
 16 20  1  0
 15  2  1  0
  2 21  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
  5 28  1  0
  9 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533071

   NVR 3-778

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: 432.40

Molecular Weight (Monoisotopic): 432.0767

AlogP: 2.64

#Rotatable Bonds: 4

Polar Surface Area: 86.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.95

CX Basic pKa: ┄

CX LogP: 2.01

CX LogD: 2.01

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: -1.92

References

1. Na HG, Imran A, Kim K, Han HS, Lee YJ, Kim MJ, Yun CS, Jung YS, Lee JY, Han SB..  (2020)  Discovery of a New Sulfonamide Hepatitis B Capsid Assembly Modulator.,  11  (2): [PMID:32071684] [10.1021/acsmedchemlett.9b00550]

2. Kuduk SD, Lam AM, Espiritu C, Vogel R, Lau V, Klumpp K, Flores OA, Hartman GD..  (2019)  SAR studies in the sulfonyl carboxamide class of HBV capsid assembly modulators.,  29  (16): [PMID:31227344] [10.1016/j.bmcl.2019.05.029]

3. Lv K, Li W, Wu S, Geng Y, Wang A, Yang L, Huang M, Chowdhury K, Li Y, Liu M..  (2020)  Amino acid prodrugs of NVR3-778: Design, synthesis and anti-HBV activity.,  30  (9): [PMID:32173194] [10.1016/j.bmcl.2020.127103]

4. Lee YH,Cha HM,Hwang JY,Park SY,Vishakantegowda AG,Imran A,Lee JY,Yi YS,Jun S,Kim GH,Kang HJ,Chung SJ,Kim M,Kim H,Han SB.  (2021)  Sulfamoylbenzamide-based Capsid Assembly Modulators for Selective Inhibition of Hepatitis B Viral Replication.,  12  (2.0): [PMID:33603970] [10.1021/acsmedchemlett.0c00606]

5. Kuduk SD,Stoops B,Alexander R,Lam AM,Espiritu C,Vogel R,Lau V,Klumpp K,Flores OA,Hartman GD.  (2021)  Identification of a new class of HBV capsid assembly modulator.,  39  [PMID:33610748] [10.1016/j.bmcl.2021.127848]

6. Li X, Zhang Z, Chen Y, Wang B, Yang G, Xu X, Yechao B, Bai D, Feng B, Mao Y, Feng J, Bai C, He F, Tao W..  (2022)  Discovery of SHR5133, a Highly Potent and Novel HBV Capsid Assembly Modulator.,  13  (3.0): [PMID:35300087] [10.1021/acsmedchemlett.2c00002]

7. Cole AG, Kultgen SG, Mani N, Ardzinski A, Fan KY, Thi EP, Dorsey BD, Stever K, Chiu T, Tang S, Daly O, Phelps JR, Harasym T, Olland A, Suto RK, Sofia MJ..  (2022)  The identification of highly efficacious functionalised tetrahydrocyclopenta[c]pyrroles as inhibitors of HBV viral replication through modulation of HBV capsid assembly.,  13  (3.0): [PMID:35434625] [10.1039/d1md00318f]

8. Ivanova Bencheva L, Donnici L, Ferrante L, Prandi A, Sinisi R, De Matteo M, Randazzo P, Conti M, Di Lucia P, Bono E, Giustini L, Vittoria Orsale M, Patsilinakos A, Monteagudo E, Iannacone M, Summa V, Guidotti LG, De Francesco R, Di Fabio R..  (2022)  Discovery and antiviral profile of new sulfamoylbenzamide derivatives as HBV capsid assembly modulators.,  73  [PMID:35868496] [10.1016/j.bmcl.2022.128904]

9. Ren Y, Ma Y, Cherukupalli S, Tavis JE, Menéndez-Arias L, Liu X, Zhan P..  (2020)  Discovery and optimization of benzenesulfonamides-based hepatitis B virus capsid modulators via contemporary medicinal chemistry strategies.,  206  [PMID:32949990] [10.1016/j.ejmech.2020.112714]

Source

Source(1):

• Scientific Literature