(1R,2S)-(2-(4-Methoxyphenyl)quinolin-4-yl)(piperidin-2-yl)-methanol Hydrochloride

ID: ALA2036070

PubChem CID: 57384770

Max Phase: Preclinical

Molecular Formula: C22H25ClN2O2

Molecular Weight: 348.45

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: COc1ccc(-c2cc([C@@H](O)[C@@H]3CCCCN3)c3ccccc3n2)cc1.Cl

Standard InChI: InChI=1S/C22H24N2O2.ClH/c1-26-16-11-9-15(10-12-16)21-14-18(17-6-2-3-7-19(17)24-21)22(25)20-8-4-5-13-23-20;/h2-3,6-7,9-12,14,20,22-23,25H,4-5,8,13H2,1H3;1H/t20-,22+;/m0./s1

Standard InChI Key: XDCQPCFYXQGEGY-IKGOIYPNSA-N

Molfile:

     RDKit          2D

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    3.3439   -9.9198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -8.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -9.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148   -9.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3148   -8.0446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0280   -8.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264   -9.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7384   -9.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4484   -9.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4460   -8.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -8.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1126   -8.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1137   -7.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8296   -6.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -7.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5399   -8.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8234   -8.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581   -6.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616   -5.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3160  -10.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3989  -10.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322  -10.9310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1182  -10.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8311  -10.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341  -11.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1181  -12.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3991  -11.7564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3070  -11.3429    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
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  2 12  1  0
  2  5  2  0
 15 18  1  0
  8  9  2  0
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  3  4  2  0
  4 20  1  0
  9 10  1  0
 20 21  1  0
  4  7  1  0
 20 22  1  1
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 10 11  2  0
 11  6  1  0
  6  5  1  0
 12 13  2  0
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  2  3  1  0
 21 28  1  6
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  6  7  2  0
M  END

Associated Targets(Human)

ABCB1 Tchem P-glycoprotein 1 (14716 Activities)

Discover Target: ABCB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MDA-MB-231 (73002 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ASF1A Tchem Histone chaperone ASF1A (46 Activities)

Discover Target: ASF1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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: 348.45	Molecular Weight (Monoisotopic): 348.1838	AlogP: 4.09	#Rotatable Bonds: 4
Polar Surface Area: 54.38	Molecular Species: BASE	HBA: 4	HBD: 2
#RO5 Violations: ┄	HBA (Lipinski): 4	HBD (Lipinski): 2	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 13.87	CX Basic pKa: 9.54	CX LogP: 3.84	CX LogD: 1.74
Aromatic Rings: 3	Heavy Atoms: 26	QED Weighted: 0.75	Np Likeness Score: 0.05

References

1. Duan Z, Li X, Huang H, Yuan W, Zheng SL, Liu X, Zhang Z, Choy E, Harmon D, Mankin H, Hornicek F.. (2012) Synthesis and evaluation of (2-(4-methoxyphenyl)-4-quinolinyl)(2-piperidinyl)methanol (NSC23925) isomers to reverse multidrug resistance in cancer., 55 (7): [PMID:22400811] [10.1021/jm300117u]
2. Miknis GF, Stevens SJ, Smith LE, Ostrov DA, Churchill ME.. (2015) Development of novel Asf1-H3/H4 inhibitors., 25 (4): [PMID:25582598] [10.1016/j.bmcl.2014.11.067]
3. Leonessa, Fabio F and 6 more authors. 2002-01-17 C-7 analogues of progesterone as potent inhibitors of the P-glycoprotein efflux pump. [PMID:11784143]
4. Broccatelli, Fabio and 6 more authors. 2011-03-24 A novel approach for predicting P-glycoprotein (ABCB1) inhibition using molecular interaction fields. [PMID:21341745]
5. Kinghorn, A Douglas; Pan, Li; Fletcher, Joshua N and Chai, Heebyung. 2011-06-24 The relevance of higher plants in lead compound discovery programs. [PMID:21650152]
6. Jabeen, Ishrat; Pleban, Karin; Rinner, Uwe; Chiba, Peter and Ecker, Gerhard F. 2012-04-12 Structure-activity relationships, ligand efficiency, and lipophilic efficiency profiles of benzophenone-type inhibitors of the multidrug transporter P-glycoprotein. [PMID:22452412]
7. Gangjee, Aleem and 7 more authors. 2013-02-15 Synthesis of N(4)-(substituted phenyl)-N(4)-alkyl/desalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines and identification of new microtubule disrupting compounds that are effective against multidrug resistant cells. [PMID:23332369]
8. Gangjee, Aleem and 5 more authors. 2013-09-12 Structure-activity relationship and in vitro and in vivo evaluation of the potent cytotoxic anti-microtubule agent N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride and its analogues as antitumor agents. [PMID:23895532]
9. Hill, Jacqueline E and 6 more authors. 2014-10-23 Selenorhodamine photosensitizers for photodynamic therapy of P-glycoprotein-expressing cancer cells. [PMID:25250825]
10. Chen, Chien-Yu CY and 5 more authors. 2016-08-08 Synthesis and bioevaluation of novel benzodipyranone derivatives as P-glycoprotein inhibitors for multidrug resistance reversal agents. [PMID:27131064]
11. Steiger, Scott A; Li, Chun; Backos, Donald S; Reigan, Philip and Natale, N R. 2017-06-15 Dimeric isoxazolyl-1,4-dihydropyridines have enhanced binding at the multi-drug resistance transporter. [PMID:28434782]
12. Pati, Maria Laura and 7 more authors. 2018-01-20 Multifunctional thiosemicarbazones and deconstructed analogues as a strategy to study the involvement of metal chelation, Sigma-2 (σ2) receptor and P-gp protein in the cytotoxic action: In vitro and in vivo activity in pancreatic tumors. [PMID:29287249]
13. Silbermann, Katja K and 6 more authors. 2019-02-15 Novel chalcone and flavone derivatives as selective and dual inhibitors of the transport proteins ABCB1 and ABCG2. [PMID:30594677]
14. Zhu, Xuezhen and 8 more authors. 2019-09-26 Triazole Bridged Flavonoid Dimers as Potent, Nontoxic, and Highly Selective Breast Cancer Resistance Protein (BCRP/ABCG2) Inhibitors. [PMID:31465686]
15. Agrawal, Neha and 5 more authors. 2020-03-12 Potential Tools for Eradicating HIV Reservoirs in the Brain: Development of Trojan Horse Prodrugs for the Inhibition of P-Glycoprotein with Anti-HIV-1 Activity. [PMID:31505928]

(1R,2S)-(2-(4-Methoxyphenyl)quinolin-4-yl)(piperidin-2-yl)-methanol Hydrochloride

Names and Identifiers

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source