ID: ALA179166

Max Phase: Preclinical

Molecular Formula: Na3O4V

Molecular Weight: 183.91

Molecule Type: Small molecule

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: 183.91

Molecular Weight (Monoisotopic): 182.8961

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Sharon A, Pratap R, Tripathi B, Srivastava AK, Maulik PR, Ram VJ..  (2005)  Biaryls and heterobiaryls as alpha-glucosidase and protein tyrosine phosphatase inhibitors.,  15  (5): [PMID:15713383] [10.1016/j.bmcl.2005.01.036]

2. Dixit M, Tripathi BK, Srivastava AK, Goel A..  (2005)  Synthesis of functionalized acetophenones as protein tyrosine phosphatase 1B inhibitors.,  15  (14): [PMID:15951172] [10.1016/j.bmcl.2005.05.024]

3. Dixit M, Tripathi BK, Tamrakar AK, Srivastava AK, Kumar B, Goel A..  (2007)  Synthesis of benzofuran scaffold-based potential PTP-1B inhibitors.,  15  (2): [PMID:17095232] [10.1016/j.bmc.2006.10.053]

4. Singh FV, Parihar A, Chaurasia S, Singh AB, Singh SP, Tamrakar AK, Srivastava AK, Goel A..  (2009)  5,6-Diarylanthranilo-1,3-dinitriles as a new class of antihyperglycemic agents.,  19  (8): [PMID:19303291] [10.1016/j.bmcl.2009.02.118]

5. Kumar A, Maurya RA, Sharma S, Ahmad P, Singh AB, Bhatia G, Srivastava AK..  (2009)  Pyranocoumarins: a new class of anti-hyperglycemic and anti-dyslipidemic agents.,  19  (22): [PMID:19811915] [10.1016/j.bmcl.2009.09.031]

6. Kumar A, Sharma S, Tripathi VD, Maurya RA, Srivastava SP, Bhatia G, Tamrakar AK, Srivastava AK..  (2010)  Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents.,  18  (11): [PMID:20471838] [10.1016/j.bmc.2009.11.061]

7. Qian S, Li H, Chen Y, Zhang W, Yang S, Wu Y..  (2010)  Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B.,  73  (11): [PMID:20964318] [10.1021/np100064m]

8. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

9. PubChem BioAssay data set, 

10. Gu X, Ren Z, Tang X, Peng H, Zhao Q, Lai Y, Peng S, Zhang Y..  (2012)  Synthesis and biological evaluation of novel bifendate derivatives bearing 6,7-dihydro-dibenzo[c,e]azepine scaffold as potent P-glycoprotein inhibitors.,  51  [PMID:22405646] [10.1016/j.ejmech.2012.02.034]

11. Gu X, Ren Z, Tang X, Peng H, Ma Y, Lai Y, Peng S, Zhang Y..  (2012)  Synthesis and biological evaluation of bifendate-chalcone hybrids as a new class of potential P-glycoprotein inhibitors.,  20  (8): [PMID:22429509] [10.1016/j.bmc.2012.02.050]

12. Liu J, Jiang F, Jin Y, Zhang Y, Liu J, Liu W, Fu L..  (2012)  Design, synthesis, and evaluation of 2-substituted ethenesulfonic acid ester derivatives as protein tyrosine phosphatase 1B inhibitors.,  57  [PMID:23043764] [10.1016/j.ejmech.2012.09.015]

13. Kumar A, Sharma S, Gupta LP, Ahmad P, Srivastava SP, Rahuja N, Tamrakar AK, Srivastava AK..  (2012)  Synthesis of propiophenone derivatives as new class of antidiabetic agents reducing body weight in db/db mice.,  20  (6): [PMID:22341243] [10.1016/j.bmc.2011.12.027]

14. Dai HL, Gao LX, Yang Y, Li JY, Cheng JG, Li J, Wen R, Peng YQ, Zheng JB..  (2012)  Discovery of di-indolinone as a novel scaffold for protein tyrosine phosphatase 1B inhibitors.,  22  (24): [PMID:23122522] [10.1016/j.bmcl.2012.10.054]

15. Liu QC, Guo TT, Zhang L, Yu Y, Wang P, Yang JF, Li YX..  (2013)  Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors.,  63  [PMID:23531458] [10.1016/j.ejmech.2013.03.001]

16. Chandrasekharappa AP, Badiger SE, Dubey PK, Panigrahi SK, Manukonda SR..  (2013)  Design and synthesis of 2-substituted benzoxazoles as novel PTP1B inhibitors.,  23  (9): [PMID:23528300] [10.1016/j.bmcl.2013.02.109]

17. Madabhushi S, Chinthala N, Kanwal A, Kaur G, Banerjee SK.  (2013)  Synthesis and characterization of 2-(4-((1-alkyl or aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)naphtho[1,2-d]oxazoles for protein tyrosine phosphatase 1B inhibitory activity,  [10.1007/s00044-013-0784-0]

18. Liu Q, Guo T, Li D, Li F, Li W..  (2014)  Synthesis and evaluation of several oleanolic acid glycoconjugates as protein tyrosine phosphatase 1B inhibitors.,  79  [PMID:24721313] [10.1016/j.ejmech.2014.03.080]

19. Li H, Jiang J, Liu Z, Lin S, Xia G, Xia X, Ding B, He L, Lu Y, She Z..  (2014)  Peniphenones A-D from the mangrove fungus Penicillium dipodomyicola HN4-3A as inhibitors of Mycobacterium tuberculosis phosphatase MptpB.,  77  (4): [PMID:24597756] [10.1021/np400880w]

20. Wang WL, Huang C, Gao LX, Tang CL, Wang JQ, Wu MC, Sheng L, Chen HJ, Nan FJ, Li JY, Li J, Feng B..  (2014)  Synthesis and biological evaluation of novel bis-aromatic amides as novel PTP1B inhibitors.,  24  (8): [PMID:24684845] [10.1016/j.bmcl.2014.03.015]

21. Zeng K, He YN, Yang D, Cao JQ, Xia XC, Zhang SJ, Bi XL, Zhao YQ..  (2014)  New compounds from acid hydrolyzed products of the fruits of Momordica charantia L. and their inhibitory activity against protein tyrosine phosphatas 1B.,  81  [PMID:24836069] [10.1016/j.ejmech.2014.01.066]

22. Yang P, Liu DQ, Liang TJ, Li J, Zhang HY, Liu AH, Guo YW, Mao SC..  (2015)  Bioactive constituents from the green alga Caulerpa racemosa.,  23  (1): [PMID:25497963] [10.1016/j.bmc.2014.11.031]

23. Li Y, Yu Y, Jin K, Gao L, Luo T, Sheng L, Shao X, Li J..  (2014)  Synthesis and biological evaluation of novel thiadiazole amides as potent Cdc25B and PTP1B inhibitors.,  24  (17): [PMID:25124112] [10.1016/j.bmcl.2014.07.055]

24. Du Y, Ling H, Zhang M, Shen J, Li Q..  (2015)  Discovery of novel, potent, selective and cellular active ADC type PTP1B inhibitors via fragment-docking-oriented de novel design.,  23  (15): [PMID:26100442] [10.1016/j.bmc.2015.05.032]

25. Liu P, Du Y, Song L, Shen J, Li Q..  (2015)  Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic.,  23  (21): [PMID:26481657] [10.1016/j.bmc.2015.09.024]

26. Lee HS, Ku B, Park TH, Park H, Choi JK, Chang KT, Kim CH, Ryu SE, Kim SJ..  (2016)  Identification of novel protein tyrosine phosphatase sigma inhibitors promoting neurite extension.,  26  (1): [PMID:26602279] [10.1016/j.bmcl.2015.11.026]

27. Doan P, Karjalainen A, Chandraseelan JG, Sandberg O, Yli-Harja O, Rosholm T, Franzen R, Candeias NR, Kandhavelu M..  (2016)  Synthesis and biological screening for cytotoxic activity of N-substituted indolines and morpholines.,  120  [PMID:27214140] [10.1016/j.ejmech.2016.05.024]

28. Stacy AE, Palanimuthu D, Bernhardt PV, Kalinowski DS, Jansson PJ, Richardson DR..  (2016)  Structure-Activity Relationships of Di-2-pyridylketone, 2-Benzoylpyridine, and 2-Acetylpyridine Thiosemicarbazones for Overcoming Pgp-Mediated Drug Resistance.,  59  (18): [PMID:27524608] [10.1021/acs.jmedchem.6b01050]

29. Meng G, Zheng M, Wang M, Tong J, Ge W, Zhang J, Zheng A, Li J, Gao L, Li J..  (2016)  Design and synthesis of new potent PTP1B inhibitors with the skeleton of 2-substituted imino-3-substituted-5-heteroarylidene-1,3-thiazolidine-4-one: Part I.,  122  [PMID:27526040] [10.1016/j.ejmech.2016.05.060]

30. DrugMatrix,  [10.6019/CHEMBL3885881]

31. Gu X, Huang Z, Ren Z, Tang X, Xue R, Luo X, Peng S, Peng H, Lu B, Tian J, Zhang Y..  (2017)  Potent Inhibition of Nitric Oxide-Releasing Bifendate Derivatives against Drug-Resistant K562/A02 Cells in Vitro and in Vivo.,  60  (3): [PMID:28068095] [10.1021/acs.jmedchem.6b01075]

32. Abdjul DB, Yamazaki H, Kanno SI, Wewengkang DS, Rotinsulu H, Sumilat DA, Ukai K, Kapojos MM, Namikoshi M..  (2017)  Furanoterpenes, new types of protein tyrosine phosphatase 1B inhibitors, from two Indonesian marine sponges, Ircinia and Spongia spp.,  27  (5): [PMID:28189419] [10.1016/j.bmcl.2017.01.071]

33. Yang F, Xie F, Zhang Y, Xia Y, Liu W, Jiang F, Lam C, Qiao Y, Xie D, Li J, Fu L..  (2017)  Y-shaped bis-arylethenesulfonic acid esters: Potential potent and membrane permeable protein tyrosine phosphatase 1B inhibitors.,  27  (10): [PMID:28372909] [10.1016/j.bmcl.2017.03.060]

34. Du Y, Zhang Y, Ling H, Li Q, Shen J..  (2018)  Discovery of novel high potent and cellular active ADC type PTP1B inhibitors with selectivity over TC-PTP via modification interacting with C site.,  144  [PMID:29289892] [10.1016/j.ejmech.2017.12.064]

35. Wang WL, Chen XY, Gao Y, Gao LX, Sheng L, Zhu J, Xu L, Ding ZZ, Zhang C, Li JY, Li J, Zhou YB..  (2017)  Benzo[c][1,2,5]thiadiazole derivatives: A new class of potent Src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2) inhibitors.,  27  (23): [PMID:29100798] [10.1016/j.bmcl.2017.10.059]

36. Latacz G, Lubelska A, Jastrzębska-Więsek M, Partyka A, Kucwaj-Brysz K, Wesołowska A, Kieć-Kononowicz K, Handzlik J..  (2018)  MF-8, a novel promising arylpiperazine-hydantoin based 5-HT7 receptor antagonist: In vitro drug-likeness studies and in vivo pharmacological evaluation.,  28  (5): [PMID:29439902] [10.1016/j.bmcl.2018.02.003]

37. Pompermaier L, Heiss EH, Alilou M, Mayr F, Monizi M, Lautenschlaeger T, Schuster D, Schwaiger S, Stuppner H..  (2018)  Dihydrochalcone Glucosides from the Subaerial Parts of Thonningia sanguinea and Their in Vitro PTP1B Inhibitory Activities.,  81  (9): [PMID:30207720] [10.1021/acs.jnatprod.8b00450]

38. Tautermann CS, Binder F, Büttner FH, Eickmeier C, Fiegen D, Gross U, Grundl MA, Heilker R, Hobson S, Hoerer S, Luippold A, Mack V, Montel F, Peters S, Bhattacharya S, Vaidehi N, Schnapp G, Thamm S, Zeeb M..  (2019)  Allosteric Activation of Striatal-Enriched Protein Tyrosine Phosphatase (STEP, PTPN5) by a Fragment-like Molecule.,  62  (1): [PMID:30207464] [10.1021/acs.jmedchem.8b00857]

39. Sun L, Wang P, Xu L, Gao L, Li J, Piao H..  (2019)  Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors.,  29  (10): [PMID:30910462] [10.1016/j.bmcl.2019.03.023]

40. Liu H, Sun D, Du H, Zheng C, Li J, Piao H, Li J, Sun L..  (2019)  Synthesis and biological evaluation of tryptophan-derived rhodanine derivatives as PTP1B inhibitors and anti-bacterial agents.,  172  [PMID:30978561] [10.1016/j.ejmech.2019.03.059]

41. Chen M, Wang K, Zhang Y, Zhang M, Ma Y, Sun H, Jin Z, Zheng H, Jiang H, Yu P, Zhang Y, Sun H..  (2019)  New insights into the biological activities of Chrysanthemum morifolium: Natural flavonoids alleviate diabetes by targeting α-glucosidase and the PTP-1B signaling pathway.,  178  [PMID:31176093] [10.1016/j.ejmech.2019.05.083]

42. Lu X, Wu L, Liu X, Wang S, Zhang C..  (2019)  BH3 mimetics derived from Bim-BH3 domain core region show PTP1B inhibitory activity.,  29  (2): [PMID:30501963] [10.1016/j.bmcl.2018.11.047]

43. Li X, Xu Q, Li C, Luo J, Li X, Wang L, Jiang B, Shi D..  (2019)  Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors.,  166  [PMID:30711829] [10.1016/j.ejmech.2019.01.057]

44. Peterková L, Kmoníčková E, Ruml T, Rimpelová S..  (2020)  Sarco/Endoplasmic Reticulum Calcium ATPase Inhibitors: Beyond Anticancer Perspective.,  63  (5): [PMID:32030976] [10.1021/acs.jmedchem.9b01509]

45. Zhou LM, Kong FD, Fan P, Ma QY, Xie QY, Li JH, Zheng HZ, Zheng ZH, Yuan JZ, Dai HF, Luo DQ, Zhao YX..  (2019)  Indole-Diterpenoids with Protein Tyrosine Phosphatase Inhibitory Activities from the Marine-Derived Fungus Penicillium sp. KFD28.,  82  (9): [PMID:31469560] [10.1021/acs.jnatprod.9b00620]

46.  (2018)  Small molecule antagonists of dusp5 and methods of use, 

47.  (2015)  Small molecule inhibitors of Dusp6 and uses therefor, 

48.  (2012)  Inhibitors of eya2, 

49. Xie F, Yang F, Liang Y, Li L, Xia Y, Jiang F, Liu W, Qi Y, Chowdhury SR, Xie D, Fu L..  (2019)  Investigation of stereoisomeric bisarylethenesulfonic acid esters for discovering potent and selective PTP1B inhibitors.,  164  [PMID:30611982] [10.1016/j.ejmech.2018.12.032]

50. Ai Y, Zhu B, Ren C, Kang F, Li J, Huang Z, Lai Y, Peng S, Ding K, Tian J, Zhang Y..  (2016)  Discovery of New Monocarbonyl Ligustrazine-Curcumin Hybrids for Intervention of Drug-Sensitive and Drug-Resistant Lung Cancer.,  59  (5): [PMID:26891099] [10.1021/acs.jmedchem.5b01203]

51. Laev SS, Salakhutdinov NF, Lavrik OI..  (2016)  Tyrosyl-DNA phosphodiesterase inhibitors: Progress and potential.,  24  (21): [PMID:27687971] [10.1016/j.bmc.2016.09.045]

52. Nguyen TA, Ha MT, Park SE, Choi JS, Min BS, Kim JA..  (2020)  Stilbenes with Potent Protein Tyrosine Phosphatase-1B Inhibitory Activity from the Roots of Polygonum multiflorum.,  83  (2): [PMID:31944695] [10.1021/acs.jnatprod.9b00777]

53. Huo C, Zheng Z, Xu Y, Ding Y, Zheng H, Mu Y, Niu Y, Gao J, Lu X..  (2020)  Naphthacemycins from a Streptomyces sp. as Protein-Tyrosine Phosphatase Inhibitors.,  83  (5): [PMID:32298122] [10.1021/acs.jnatprod.9b00417]

54. Satheeshkumar R, Zhu R, Feng B, Huang C, Gao Y, Gao LX, Shen C, Hou TJ, Xu L, Li J, Zhu YL, Zhou YB, Wang WL..  (2020)  Synthesis and biological evaluation of heterocyclic bis-aryl amides as novel Src homology 2 domain containing protein tyrosine phosphatase-2 (SHP2) inhibitors.,  30  (11): [PMID:32273218] [10.1016/j.bmcl.2020.127170]

55. Zhang Z, Shang ZP, Jiang Y, Qu ZX, Yang RY, Zhang J, Lin YX, Zhao F..  (2022)  Selective Inhibition of PTP1B by New Anthraquinone Glycosides from Knoxia valerianoides.,  85  (12.0): [PMID:36399709] [10.1021/acs.jnatprod.2c00879]

56. Li N, Li X, Deng M, Zhu F, Wang Z, Sheng R, Wu W, Guo R..  (2023)  Isosteviol derivatives as protein tyrosine Phosphatase-1B inhibitors: Synthesis, biological evaluation and molecular docking.,  83  [PMID:36963270] [10.1016/j.bmc.2023.117240]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• DrugMatrix
• Patent Bioactivity Data