ID: ALA219728

Max Phase: Preclinical

Molecular Formula: C20H22N4

Molecular Weight: 318.42

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  CN(C)CCCNc1c2ccccc2nc2c1[nH]c1ccccc12

Standard InChI:  InChI=1S/C20H22N4/c1-24(2)13-7-12-21-18-14-8-3-5-10-16(14)22-19-15-9-4-6-11-17(15)23-20(18)19/h3-6,8-11,23H,7,12-13H2,1-2H3,(H,21,22)

Standard InChI Key:  CTDCVGDSVHUYMA-UHFFFAOYSA-N

Associated Targets(Human)

Telomerase reverse transcriptase 2428 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Ramos 1218 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

CA46 271 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

HeLa 62764 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

HL-60 67320 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

K562 73714 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

MGC-803 6426 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Bel-7402 4577 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

DNA topoisomerase I 7553 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Tyrosyl-DNA phosphodiesterase 1 345557 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

dsDNA 365 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

HCT-116 91556 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

CCRF-CEM 65223 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

DU-145 51482 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

A549 127892 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Huh-7 12904 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

quadruplex DNA 2700 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

SW-620 52400 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 318.42Molecular Weight (Monoisotopic): 318.1844AlogP: 4.23#Rotatable Bonds: 5
Polar Surface Area: 43.95Molecular Species: BASEHBA: 3HBD: 2
#RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
CX Acidic pKa: 13.78CX Basic pKa: 9.41CX LogP: 3.19CX LogD: 0.66
Aromatic Rings: 4Heavy Atoms: 24QED Weighted: 0.54Np Likeness Score: -0.73

References

1. Ou TM, Lu YJ, Zhang C, Huang ZS, Wang XD, Tan JH, Chen Y, Ma DL, Wong KY, Tang JC, Chan AS, Gu LQ..  (2007)  Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc by quindoline derivatives.,  50  (7): [PMID:17346034] [10.1021/jm0610088]
2. 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]
3. Lu YJ, Ou TM, Tan JH, Hou JQ, Shao WY, Peng D, Sun N, Wang XD, Wu WB, Bu XZ, Huang ZS, Ma DL, Wong KY, Gu LQ..  (2008)  5-N-methylated quindoline derivatives as telomeric g-quadruplex stabilizing ligands: effects of 5-N positive charge on quadruplex binding affinity and cell proliferation.,  51  (20): [PMID:18821749] [10.1021/jm800497p]
4. Tan JH, Ou TM, Hou JQ, Lu YJ, Huang SL, Luo HB, Wu JY, Huang ZS, Wong KY, Gu LQ..  (2009)  Isaindigotone derivatives: a new class of highly selective ligands for telomeric G-quadruplex DNA.,  52  (9): [PMID:19354252] [10.1021/jm801600m]
5. Ou TM, Lin J, Lu YJ, Hou JQ, Tan JH, Chen SH, Li Z, Li YP, Li D, Gu LQ, Huang ZS..  (2011)  Inhibition of cell proliferation by quindoline derivative (SYUIQ-05) through its preferential interaction with c-myc promoter G-quadruplex.,  54  (16): [PMID:21774525] [10.1021/jm200062u]
6. Li Z, Tan JH, He JH, Long Y, Ou TM, Li D, Gu LQ, Huang ZS..  (2012)  Disubstituted quinazoline derivatives as a new type of highly selective ligands for telomeric G-quadruplex DNA.,  47  [PMID:22104971] [10.1016/j.ejmech.2011.10.057]
7. He JH, Liu HY, Li Z, Tan JH, Ou TM, Huang SL, An LK, Li D, Gu LQ, Huang ZS..  (2013)  New quinazoline derivatives for telomeric G-quadruplex DNA: effects of an added phenyl group on quadruplex binding ability.,  63  [PMID:23454529] [10.1016/j.ejmech.2013.01.051]
8. Artese A, Costa G, Distinto S, Moraca F, Ortuso F, Parrotta L, Alcaro S..  (2013)  Toward the design of new DNA G-quadruplex ligands through rational analysis of polymorphism and binding data.,  68  [PMID:23974014] [10.1016/j.ejmech.2013.07.022]
9. Liu HY, Chen AC, Yin QK, Li Z, Huang SM, Du G, He JH, Zan LP, Wang SK, Xu YH, Tan JH, Ou TM, Li D, Gu LQ, Huang ZS..  (2017)  New Disubstituted Quindoline Derivatives Inhibiting Burkitt's Lymphoma Cell Proliferation by Impeding c-MYC Transcription.,  60  (13): [PMID:28603988] [10.1021/acs.jmedchem.7b00099]
10. Zhang XR, Wang HW, Tang WL, Zhang Y, Yang H, Hu DX, Ravji A, Marchand C, Kiselev E, Ofori-Atta K, Agama K, Pommier Y, An LK..  (2018)  Discovery, Synthesis, and Evaluation of Oxynitidine Derivatives as Dual Inhibitors of DNA Topoisomerase IB (TOP1) and Tyrosyl-DNA Phosphodiesterase 1 (TDP1), and Potential Antitumor Agents.,  61  (22): [PMID:30336023] [10.1021/acs.jmedchem.8b00639]
11. Che T, Chen SB, Tu JL, Wang B, Wang YQ, Zhang Y, Wang J, Wang ZQ, Zhang ZP, Ou TM, Zhao Y, Tan JH, Huang ZS..  (2018)  Discovery of Novel Schizocommunin Derivatives as Telomeric G-Quadruplex Ligands That Trigger Telomere Dysfunction and the Deoxyribonucleic Acid (DNA) Damage Response.,  61  (8): [PMID:29618208] [10.1021/acs.jmedchem.7b01615]
12. Mendes E, Bahls B, Aljnadi IM, Paulo A..  (2022)  Indoloquinolines as scaffolds for the design of potent G-quadruplex ligands.,  72  [PMID:35716866] [10.1016/j.bmcl.2022.128862]
13. 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]

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