ID: ALA330383

Max Phase: Preclinical

Molecular Formula: C19H29N3O

Molecular Weight: 315.46

Molecule Type: Small molecule

Representations

Synonyms (1): 2-Tert-Butylprimaquine
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(NC(C)CCCN)c2nc(C(C)(C)C)ccc2c1

Standard InChI:  InChI=1S/C19H29N3O/c1-13(7-6-10-20)21-16-12-15(23-5)11-14-8-9-17(19(2,3)4)22-18(14)16/h8-9,11-13,21H,6-7,10,20H2,1-5H3

Standard InChI Key:  IDSOIRUIKYGAHY-UHFFFAOYSA-N

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

Properties

Molecular Weight: 315.46

Molecular Weight (Monoisotopic): 315.2311

AlogP: 4.08

#Rotatable Bonds: 6

Polar Surface Area: 60.17

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 10.20

CX LogP: 3.57

CX LogD: 0.97

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.48

References

1. Jain M, Vangapandu S, Sachdeva S, Singh S, Singh PP, Jena GB, Tikoo K, Ramarao P, Kaul CL, Jain R..  (2004)  Discovery of a bulky 2-tert-butyl group containing primaquine analogue that exhibits potent blood-schizontocidal antimalarial activities and complete elimination of methemoglobin toxicity.,  47  (2): [PMID:14711300] [10.1021/jm0304562]

2. Huy NT, Mizunuma K, Kaur K, Nhien NT, Jain M, Uyen DT, Harada S, Jain R, Kamei K..  (2007)  2-tert-butyl-8-quinolinamines exhibit potent blood schizontocidal antimalarial activity via inhibition of heme crystallization.,  51  (8): [PMID:17562796] [10.1128/aac.00288-07]

3. Kaur K, Jain M, Reddy RP, Jain R..  (2010)  Quinolines and structurally related heterocycles as antimalarials.,  45  (8): [PMID:20466465] [10.1016/j.ejmech.2010.04.011]

4. Kaur K, Jain M, Khan SI, Jacob MR, Tekwani BL, Singh S, Singh PP, Jain R..  (2011)  Synthesis, antiprotozoal, antimicrobial, β-hematin inhibition, cytotoxicity and methemoglobin (MetHb) formation activities of bis(8-aminoquinolines).,  19  (1): [PMID:21172735] [10.1016/j.bmc.2010.11.036]

5. Kaur K, Jain M, Khan SI, Jacob MR, Tekwani BL, Singh S, Singh PP, Jain R..  (2012)  Amino acid, dipeptide and pseudodipeptide conjugates of ring-substituted 8-aminoquinolines: synthesis and evaluation of anti-infective, β-haematin inhibition and cytotoxic activities.,  52  [PMID:22483965] [10.1016/j.ejmech.2012.03.019]

6. Hu YQ, Gao C, Zhang S, Xu L, Xu Z, Feng LS, Wu X, Zhao F..  (2017)  Quinoline hybrids and their antiplasmodial and antimalarial activities.,  139  [PMID:28800458] [10.1016/j.ejmech.2017.07.061]

Source

Source(1):

• Scientific Literature