ID: ALA224248

Max Phase: Preclinical

Molecular Formula: C15H10N2

Molecular Weight: 218.26

Molecule Type: Small molecule

Representations

Synonyms (2): 10H-Indolo[3,2-B]Quinoline | Quindoline
Synonyms from Alternative Forms(2):

Canonical SMILES:  c1ccc2nc3c(cc2c1)[nH]c1ccccc13

Standard InChI:  InChI=1S/C15H10N2/c1-3-7-12-10(5-1)9-14-15(17-12)11-6-2-4-8-13(11)16-14/h1-9,16H

Standard InChI Key:  QOAKRWLMTKEDDL-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 218.26

Molecular Weight (Monoisotopic): 218.0844

AlogP: 3.87

#Rotatable Bonds: 0

Polar Surface Area: 28.68

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.91

CX Basic pKa: 4.50

CX LogP: 3.63

CX LogD: 3.63

Aromatic Rings: 4

Heavy Atoms: 17

QED Weighted: 0.48

Np Likeness Score: -0.24

References

1. Caprio V, Guyen B, Opoku-Boahen Y, Mann J, Gowan SM, Kelland LM, Read MA, Neidle S..  (2000)  A novel inhibitor of human telomerase derived from 10H-indolo[3,2-b]quinoline.,  10  (18): [PMID:10999471] [10.1016/s0960-894x(00)00378-4]

2. Wright CW, Addae-Kyereme J, Breen AG, Brown JE, Cox MF, Croft SL, Gökçek Y, Kendrick H, Phillips RM, Pollet PL..  (2001)  Synthesis and evaluation of cryptolepine analogues for their potential as new antimalarial agents.,  44  (19): [PMID:11543688] [10.1021/jm010929+]

3. Arzel E, Rocca P, Grellier P, Labaeïd M, Frappier F, Guéritte F, Gaspard C, Marsais F, Godard A, Quéguiner G..  (2001)  New synthesis of benzo-delta-carbolines, cryptolepines, and their salts: in vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of delta-carbolines, benzo-delta-carbolines, and cryptolepines.,  44  (6): [PMID:11300877] [10.1021/jm0010419]

4. Zhou JL, Lu YJ, Ou TM, Zhou JM, Huang ZS, Zhu XF, Du CJ, Bu XZ, Ma L, Gu LQ, Li YM, Chan AS..  (2005)  Synthesis and evaluation of quindoline derivatives as G-quadruplex inducing and stabilizing ligands and potential inhibitors of telomerase.,  48  (23): [PMID:16279791] [10.1021/jm050041b]

5. Cimanga K, De Bruyne T, Pieters L, Vlietinck AJ, Turger CA..  (1997)  In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta.,  60  (7): [PMID:9249972] [10.1021/np9605246]

6. Yang SW, Abdel-Kader M, Malone S, Werkhoven MC, Wisse JH, Bursuker I, Neddermann K, Fairchild C, Raventos-Suarez C, Menendez AT, Lane K, Kingston DG..  (1999)  Synthesis and biological evaluation of analogues of cryptolepine, an alkaloid isolated from the Suriname rainforest.,  62  (7): [PMID:10425120] [10.1021/np990035g]

7. Nuthakki VK, Mudududdla R, Bharate SB..  (2022)  Role of basic aminoalkyl chains in the lead optimization of Indoloquinoline alkaloids.,  227  [PMID:34710743] [10.1016/j.ejmech.2021.113938]

Source

Source(1):

• Scientific Literature