4-(2,6-Dimethyl-phenyl)-1-methyl-1,2,3,6-tetrahydro-pyridine

ID: ALA98104

PubChem CID: 44330964

Max Phase: Preclinical

Molecular Formula: C14H19N

Molecular Weight: 201.31

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: Cc1cccc(C)c1C1=CCN(C)CC1

Standard InChI: InChI=1S/C14H19N/c1-11-5-4-6-12(2)14(11)13-7-9-15(3)10-8-13/h4-7H,8-10H2,1-3H3

Standard InChI Key: AKODWPTUHCBVGC-UHFFFAOYSA-N

Molfile:

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    5.9875   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875   -4.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875   -5.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  9  1  0
  5  1  1  0
  6  2  2  0
  7  2  1  0
  8  3  1  0
  9  5  1  0
 10  4  1  0
 11 12  1  0
 12  7  2  0
 13  6  1  0
 14  6  1  0
 15  7  1  0
  8  4  1  0
 13 11  2  0
M  END

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: 201.31	Molecular Weight (Monoisotopic): 201.1517	AlogP: 3.02	#Rotatable Bonds: 1
Polar Surface Area: 3.24	Molecular Species: NEUTRAL	HBA: 1	HBD: ┄
#RO5 Violations: ┄	HBA (Lipinski): 1	HBD (Lipinski): ┄	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: ┄	CX Basic pKa: 8.35	CX LogP: 3.38	CX LogD: 2.38
Aromatic Rings: 1	Heavy Atoms: 15	QED Weighted: 0.67	Np Likeness Score: -0.11

References

1. Good AC, Peterson SJ, Richards WG.. (1993) QSAR's from similarity matrices. Technique validation and application in the comparison of different similarity evaluation methods., 36 (20): [PMID:8411009] [10.1021/jm00072a012]
2. Wang, Eric Y EY and 9 more authors. 2006-04-06 Design, synthesis, and biological evaluation of semicarbazide-sensitive amine oxidase (SSAO) inhibitors with anti-inflammatory activity. [PMID:16570912]
3. Reck, Folkert F and 8 more authors. 2007-10-04 Novel substituted (pyridin-3-yl)phenyloxazolidinones: antibacterial agents with reduced activity against monoamine oxidase A and increased solubility. [PMID:17722903]
4. Grice, Cheryl A CA and 15 more authors. 2008-07-24 Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity. [PMID:18588282]
5. Van der Walt, Elizna M and 6 more authors. 2009-05-01 Inhibition of monoamine oxidase by (E)-styrylisatin analogues. [PMID:19342233]
6. Wichitnithad, Wisut W, O'Callaghan, James P JP, Miller, Diane B DB, Train, Brian C BC and Callery, Patrick S PS. 2011-12-15 Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines. [PMID:22078410]
7. Geldenhuys, Werner J WJ, Funk, Max O MO, Van der Schyf, Cornelis J CJ and Carroll, Richard T RT. 2012-02-01 A scaffold hopping approach to identify novel monoamine oxidase B inhibitors. [PMID:22225638]
8. Legoabe, Lesetja J LJ, Petzer, Anél A and Petzer, Jacobus P JP. 2012-03 Inhibition of monoamine oxidase by selected C6-substituted chromone derivatives. [PMID:22309913]
9. Huang, Ling L and 8 more authors. 2012-10-11 Multitarget-directed benzylideneindanone derivatives: anti-β-amyloid (Aβ) aggregation, antioxidant, metal chelation, and monoamine oxidase B (MAO-B) inhibition properties against Alzheimer's disease. [PMID:22978824]
10. Van der Walt, Mietha M MM, Terre'Blanche, Gisella G, Petzer, Anél A and Petzer, Jacobus P JP. 2012-11-01 Novel sulfanylphthalimide analogues as highly potent inhibitors of monoamine oxidase B. [PMID:23010267]
11. Van der Walt, Mietha M MM, Terre'Blanche, Gisella G, Lourens, Anna C U AC, Petzer, Anél A and Petzer, Jacobus P JP. 2012-12-15 Sulfanylphthalonitrile analogues as selective and potent inhibitors of monoamine oxidase B. [PMID:23122857]
12. Helguera, Aliuska Morales AM and 7 more authors. 2013-01 Combining QSAR classification models for predictive modeling of human monoamine oxidase inhibitors. [PMID:23207409]
13. Strydom, Belinda B, Bergh, Jacobus J JJ and Petzer, Jacobus P JP. 2013-03-01 Inhibition of monoamine oxidase by phthalide analogues. [PMID:23374869]
14. Lu, Chuanjun C and 5 more authors. 2013-04 A novel series of tacrine-selegiline hybrids with cholinesterase and monoamine oxidase inhibition activities for the treatment of Alzheimer's disease. [PMID:23454517]
15. Schmitt, Martin L and 11 more authors. 2013-09-26 Nonpeptidic propargylamines as inhibitors of lysine specific demethylase 1 (LSD1) with cellular activity. [PMID:24007511]
16. Sun, Yang Y, Chen, Jianwen J, Chen, Xuemin X, Huang, Ling L and Li, Xingshu X. 2013-12-01 Inhibition of cholinesterase and monoamine oxidase-B activity by Tacrine-Homoisoflavonoid hybrids. [PMID:24128814]
17. Bautista-Aguilera, Oscar M OM and 10 more authors. 2014-03-21 Design, synthesis, pharmacological evaluation, QSAR analysis, molecular modeling and ADMET of novel donepezil-indolyl hybrids as multipotent cholinesterase/monoamine oxidase inhibitors for the potential treatment of Alzheimer's disease. [PMID:24530494]
18. Legoabe, Lesetja J LJ, Petzer, Anél A and Petzer, Jacobus P JP. 2014-06-15 α-Tetralone derivatives as inhibitors of monoamine oxidase. [PMID:24794105]
19. Huleatt, Paul B PB and 13 more authors. 2015-02-12 Novel arylalkenylpropargylamines as neuroprotective, potent, and selective monoamine oxidase B inhibitors for the treatment of Parkinson's disease. [PMID:25627172]
20. Chirkova, Zhanna V ZV and 7 more authors. 2015-03-15 Inhibition of monoamine oxidase by indole-5,6-dicarbonitrile derivatives. [PMID:25701250]
21. Engelbrecht, Idalet I, Petzer, Jacobus P JP and Petzer, Anél A. 2015-05-01 The synthesis and evaluation of sesamol and benzodioxane derivatives as inhibitors of monoamine oxidase. [PMID:25857942]
22. Xie, Shishun S and 7 more authors. 2015-07-01 Synthesis and evaluation of selegiline derivatives as monoamine oxidase inhibitor, antioxidant and metal chelator against Alzheimer's disease. [PMID:25934229]
23. Farina, Roberta R and 13 more authors. 2015-07-23 Structure-Based Design and Optimization of Multitarget-Directed 2H-Chromen-2-one Derivatives as Potent Inhibitors of Monoamine Oxidase B and Cholinesterases. [PMID:26107513]
24. Wu, Ming-Yu MY and 9 more authors. 2016-10-04 Donepezil-like multifunctional agents: Design, synthesis, molecular modeling and biological evaluation. [PMID:26471320]
25. Papillon, Julien P N JP and 17 more authors. 2015-12-10 Discovery of N-[5-(6-Chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-ethanesulfonamide, a Cortisol-Sparing CYP11B2 Inhibitor that Lowers Aldosterone in Human Subjects. [PMID:26540564]
26. Vianello, Paola P and 16 more authors. 2016-02-25 Discovery of a Novel Inhibitor of Histone Lysine-Specific Demethylase 1A (KDM1A/LSD1) as Orally Active Antitumor Agent. [PMID:26702542]
27. Mostert, Samantha S, Petzer, Anél A and Petzer, Jacobus P JP. 2016-02-15 Inhibition of monoamine oxidase by benzoxathiolone analogues. [PMID:26821818]
28. Chirkova, Zhanna V ZV and 6 more authors. 2016-05-01 An evaluation of synthetic indole derivatives as inhibitors of monoamine oxidase. [PMID:27020523]
29. Li, Yan Y and 6 more authors. 2016-05-15 Synthesis and evaluation of 4-hydroxyl aurone derivatives as multifunctional agents for the treatment of Alzheimer's disease. [PMID:27079124]
30. Pisani, Leonardo L and 11 more authors. 2016-07-28 Exploring Basic Tail Modifications of Coumarin-Based Dual Acetylcholinesterase-Monoamine Oxidase B Inhibitors: Identification of Water-Soluble, Brain-Permeant Neuroprotective Multitarget Agents. [PMID:27347731]
31. Lee, Hyun Woo HW and 5 more authors. 2016-10-01 Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens. [PMID:27575476]
32. Nel, Magdalena S MS, Petzer, Anél A, Petzer, Jacobus P JP and Legoabe, Lesetja J LJ. 2016-10-01 2-Benzylidene-1-indanone derivatives as inhibitors of monoamine oxidase. [PMID:27578245]
33. Wang, Zhimin Z and 7 more authors. 2016-11-15 Neuroprotective effects of benzyloxy substituted small molecule monoamine oxidase B inhibitors in Parkinson's disease. [PMID:27692996]
34. Joubert, Jacques J and 5 more authors. 2017-01-05 Synthesis and evaluation of 7-substituted coumarin derivatives as multimodal monoamine oxidase-B and cholinesterase inhibitors for the treatment of Alzheimer's disease. [PMID:27744252]
35. Chaurasiya, Narayan D ND and 8 more authors. 2016-10-28 Isolation of Acacetin from Calea urticifolia with Inhibitory Properties against Human Monoamine Oxidase-A and -B. [PMID:27754693]
36. Košak, Urban U and 9 more authors. 2017-01-15 N-Propargylpiperidines with naphthalene-2-carboxamide or naphthalene-2-sulfonamide moieties: Potential multifunctional anti-Alzheimer's agents. [PMID:27908752]
37. Li, Yan Y and 9 more authors. 2017-01-15 Multitarget drug design strategy against Alzheimer's disease: Homoisoflavonoid Mannich base derivatives serve as acetylcholinesterase and monoamine oxidase B dual inhibitors with multifunctional properties. [PMID:27923535]
38. Li, Yan Y and 8 more authors. 2017-01-27 Aurone Mannich base derivatives as promising multifunctional agents with acetylcholinesterase inhibition, anti-β-amyloid aggragation and neuroprotective properties for the treatment of Alzheimer's disease. [PMID:27951485]
39. Xiao, Ganyuan G and 10 more authors. 2017-02-01 Design, synthesis and biological evaluation of 4'-aminochalcone-rivastigmine hybrids as multifunctional agents for the treatment of Alzheimer's disease. [PMID:28011206]
40. Tzvetkov, Nikolay T NT and 5 more authors. 2017-02-15 Crystal structures, binding interactions, and ADME evaluation of brain penetrant N-substituted indazole-5-carboxamides as subnanomolar, selective monoamine oxidase B and dual MAO-A/B inhibitors. [PMID:28107736]
41. Qiang, Xiaoming X and 8 more authors. 2017-02-15 DL-3-n-butylphthalide-Edaravone hybrids as novel dual inhibitors of amyloid-β aggregation and monoamine oxidases with high antioxidant potency for Alzheimer's therapy. [PMID:28131710]
42. Luo, Li L and 9 more authors. 2017-03-15 Multifunctional thioxanthone derivatives with acetylcholinesterase, monoamine oxidases and β-amyloid aggregation inhibitory activities as potential agents against Alzheimer's disease. [PMID:28237559]
43. Mostert, Samantha S, Petzer, Anél A and Petzer, Jacobus P JP. 2017-07-28 The evaluation of 1,4-benzoquinones as inhibitors of human monoamine oxidase. [PMID:28456030]
44. Yang, Hua-Li HL and 8 more authors. 2017-09-29 Design, synthesis and evaluation of coumarin-pargyline hybrids as novel dual inhibitors of monoamine oxidases and amyloid-β aggregation for the treatment of Alzheimer's disease. [PMID:28728104]
45. Fonseca, André A and 8 more authors. 2017-08-24 Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis? [PMID:28753307]
46. Duan, Ying-Chao YC and 9 more authors. 2017-11-10 Design and synthesis of tranylcypromine derivatives as novel LSD1/HDACs dual inhibitors for cancer treatment. [PMID:28987602]
47. Sang, Zhipei Z and 8 more authors. 2017-11-15 Design, synthesis and biological evaluation of 2-acetyl-5-O-(amino-alkyl)phenol derivatives as multifunctional agents for the treatment of Alzheimer's disease. [PMID:29033233]
48. Carradori, Simone S and 11 more authors. 2018-01-01 Design, synthesis and biochemical evaluation of novel multi-target inhibitors as potential anti-Parkinson agents. [PMID:29126727]
49. Xu, Yi-Xiang YX and 11 more authors. 2018-01-01 Discovery of novel propargylamine-modified 4-aminoalkyl imidazole substituted pyrimidinylthiourea derivatives as multifunctional agents for the treatment of Alzheimer's disease. [PMID:29172081]
50. Yeon, Seul Ki SK and 12 more authors. 2018-01-01 Synthesis and evaluation of biaryl derivatives for structural characterization of selective monoamine oxidase B inhibitors toward Parkinson's disease therapy. [PMID:29198609]
51. Schulz-Fincke, Johannes J and 15 more authors. 2018-01-20 Structure-activity studies on N-Substituted tranylcypromine derivatives lead to selective inhibitors of lysine specific demethylase 1 (LSD1) and potent inducers of leukemic cell differentiation. [PMID:29247860]
52. Xiao, Xuan X and 6 more authors. 2018-02-10 Design, synthesis and bioevalucation of novel 2,3-dihydro-1H-inden-1-amine derivatives as potent and selective human monoamine oxidase B inhibitors based on rasagiline. [PMID:29339253]
53. Xu, Rui R and 9 more authors. 2018-05-01 Multifunctional 5,6-dimethoxybenzo[d]isothiazol-3(2H)-one-N-alkylbenzylamine derivatives with acetylcholinesterase, monoamine oxidases and β-amyloid aggregation inhibitory activities as potential agents against Alzheimer's disease. [PMID:29500132]
54. Bautista-Aguilera, Óscar M ÓM and 9 more authors. 2018-08-09 Contilisant, a Tetratarget Small Molecule for Alzheimer's Disease Therapy Combining Cholinesterase, Monoamine Oxidase Inhibition, and H3R Antagonism with S1R Agonism Profile. [PMID:29969030]
55. Gealageas, Ronan R and 10 more authors. 2018-08-23 Development of Novel Monoamine Oxidase-B (MAO-B) Inhibitors with Reduced Blood-Brain Barrier Permeability for the Potential Management of Noncentral Nervous System (CNS) Diseases. [PMID:30016860]
56. Abid, Syed Mobasher Ali SMA and 7 more authors. 2017-02-01 Pyrazolobenzothiazine-based carbothioamides as new structural leads for the inhibition of monoamine oxidases: design, synthesis, in vitro bioevaluation and molecular docking studies. [PMID:30108763]
57. Denya, Ireen I and 7 more authors. 2018-02-01 Design, synthesis and evaluation of indole derivatives as multifunctional agents against Alzheimer's disease. [PMID:30108930]
58. Pisani, Leonardo L and 7 more authors. 2019-01-01 Investigating alkyl nitrates as nitric oxide releasing precursors of multitarget acetylcholinesterase-monoamine oxidase B inhibitors. [PMID:30366255]
59. Duan, Yingchao Y and 7 more authors. 2018-12-15 Design, synthesis and in vitro evaluation of stilbene derivatives as novel LSD1 inhibitors for AML therapy. [PMID:30448189]
60. Shetnev, Anton A and 8 more authors. 2019-01-01 Novel monoamine oxidase inhibitors based on the privileged 2-imidazoline molecular framework. [PMID:30455149]
61. Li, Shiyu S and 9 more authors. 2019-05-01 Discovery of novel 2,3-dihydro-1H-inden-1-amine derivatives as selective monoamine oxidase B inhibitors. [PMID:30833108]
62. Tao, Deng D and 7 more authors. 2019-07-01 Discovery of coumarin Mannich base derivatives as multifunctional agents against monoamine oxidase B and neuroinflammation for the treatment of Parkinson's disease. [PMID:31005056]
63. Zhang, Pengfei P, Xu, Shengtao S, Zhu, Zheying Z and Xu, Jinyi J. 2019-08-15 Multi-target design strategies for the improved treatment of Alzheimer's disease. [PMID:31103902]
64. Kumar, Bhupinder B and 8 more authors. 2019-09-01 Dipropargyl substituted diphenylpyrimidines as dual inhibitors of monoamine oxidase and acetylcholinesterase. [PMID:31151057]
65. Sang, Zhipei Z, Wang, Keren K, Shi, Jian J, Liu, Wenmin W and Tan, Zhenghuai Z. 2019-09-15 Design, synthesis, in-silico and biological evaluation of novel chalcone-O-carbamate derivatives as multifunctional agents for the treatment of Alzheimer's disease. [PMID:31229875]
66. Tzvetkov, Nikolay T NT and 10 more authors. 2019-06-19 Carboxamides vs. methanimines: Crystal structures, binding interactions, photophysical studies, and biological evaluation of (indazole-5-yl)methanimines as monoamine oxidase B and acetylcholinesterase inhibitors. [PMID:31265934]
67. Sang, Zhipei Z and 5 more authors. 2019-07-12 Design, synthesis, in-silico and biological evaluation of novel chalcone derivatives as multi-function agents for the treatment of Alzheimer's disease. [PMID:31310916]
68. Zhu, Gaofeng and 8 more authors. 2019-10-01 The development of 2-acetylphenol-donepezil hybrids as multifunctional agents for the treatment of Alzheimer's disease. [PMID:31444085]
69. Bai, Ping and 10 more authors. 2019-12-01 Development of chalcone-O-alkylamine derivatives as multifunctional agents against Alzheimer's disease. [PMID:31581002]
70. do Carmo Carreiras, Maria; Ismaili, Lhassane and Marco-Contelles, José. 2020-02-01 Propargylamine-derived multi-target directed ligands for Alzheimer's disease therapy. [PMID:31864798]
71. Sang, Zhipei and 13 more authors. 2020-05-15 Design, synthesis and biological evaluation of novel O-carbamoyl ferulamide derivatives as multi-target-directed ligands for the treatment of Alzheimer's disease. [PMID:32240904]
72. Xie, Sai-Sai and 12 more authors. 2020-09-15 Design, synthesis and biological evaluation of rasagiline-clorgyline hybrids as novel dual inhibitors of monoamine oxidase-B and amyloid-β aggregation against Alzheimer's disease. [PMID:32652406]
73. Dai, Xing-Jie and 5 more authors. 2020-12-10 Tranylcypromine Based Lysine-Specific Demethylase 1 Inhibitor: Summary and Perspective. [PMID:32931269]
74. Jismy, Badr and 7 more authors. 2021-01-01 Pyrimido[1,2-b]indazole derivatives: Selective inhibitors of human monoamine oxidase B with neuroprotective activity. [PMID:33071056]
75. Jin, Chuan-Fei; Wang, Zhi-Zheng; Chen, Kang-Zhi; Xu, Teng-Fei and Hao, Ge-Fei. 2020-12-10 Computational Fragment-Based Design Facilitates Discovery of Potent and Selective Monoamine Oxidase-B (MAO-B) Inhibitor. [PMID:33210537]
76. Mezeiova, Eva and 16 more authors. 2021-02-05 2-Propargylamino-naphthoquinone derivatives as multipotent agents for the treatment of Alzheimer's disease. [PMID:33360800]
77. Cao, Zhongcheng and 6 more authors. 2021-02-16 Novel 3-benzylidene/benzylphthalide Mannich base derivatives as potential multifunctional agents for the treatment of Alzheimer's disease. [PMID:33640707]
78. Sang, Zhipei and 5 more authors. 2021-02-23 Design, synthesis and evaluation of novel dimethylamino chalcone-O-alkylamines derivatives as potential multifunctional agents against Alzheimer's disease. [PMID:33667847]

4-(2,6-Dimethyl-phenyl)-1-methyl-1,2,3,6-tetrahydro-pyridine

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source