8-chloro-4-(4-methylpiperazin-1-yl)benzofuro[3,2-d]pyrimidine

ID: ALA1093180

Cas Number: 489402-96-2

PubChem CID: 2063135

Max Phase: Preclinical

Molecular Formula: C15H15ClN4O

Molecular Weight: 302.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ncnc3c2oc2ccc(Cl)cc23)CC1

Standard InChI:  InChI=1S/C15H15ClN4O/c1-19-4-6-20(7-5-19)15-14-13(17-9-18-15)11-8-10(16)2-3-12(11)21-14/h2-3,8-9H,4-7H2,1H3

Standard InChI Key:  VUWKQWOFKSEXGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   18.1105   -0.9687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8768   -1.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4420   -2.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2426   -2.1567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4751   -1.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9069   -0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8094   -2.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1081    0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1069   -0.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8200   -1.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8182    0.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5317    0.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5366   -0.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3264   -1.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3185    0.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8075   -0.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6275   -0.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9596    0.4535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4656    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6473    1.0265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3954    0.4196    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 12 11  2  0
 11  8  1  0
 12 13  1  0
  4  5  1  0
  5  6  1  0
  1  2  1  0
 13 14  1  0
 14 16  1  0
 15 12  1  0
  4  7  1  0
 15 16  2  0
  1  6  1  0
 16 17  1  0
  8  9  2  0
 17 18  2  0
  2  3  1  0
 18 19  1  0
  9 10  1  0
 19 20  2  0
 20 15  1  0
 17  1  1  0
 10 13  2  0
  8 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093180

   8-Chloro-4-(4-methylpiperazin-1-yl)benzofuro[3,2-d]pyrimidine

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: 302.76

Molecular Weight (Monoisotopic): 302.0934

AlogP: 2.78

#Rotatable Bonds: 1

Polar Surface Area: 45.40

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.33

CX LogP: 2.77

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -1.34

References

1. Cramp S, Dyke HJ, Higgs C, Clark DE, Gill M, Savy P, Jennings N, Price S, Lockey PM, Norman D, Porres S, Wilson F, Jones A, Ramsden N, Mangano R, Leggate D, Andersson M, Hale R..  (2010)  Identification and hit-to-lead exploration of a novel series of histamine H4 receptor inverse agonists.,  20  (8): [PMID:20299215] [10.1016/j.bmcl.2010.02.097]

2. Savall BM, Gomez L, Chavez F, Curtis M, Meduna SP, Kearney A, Dunford P, Cowden J, Thurmond RL, Grice C, Edwards JP..  (2011)  Tricyclic aminopyrimidine histamine H4 receptor antagonists.,  21  (21): [PMID:21920744] [10.1016/j.bmcl.2011.08.014]

3. Savall BM, Chavez F, Tays K, Dunford PJ, Cowden JM, Hack MD, Wolin RL, Thurmond RL, Edwards JP..  (2014)  Discovery and SAR of 6-alkyl-2,4-diaminopyrimidines as histamine H₄ receptor antagonists.,  57  (6): [PMID:24495018] [10.1021/jm401727m]

Source

Source(1):

• Scientific Literature