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[ CAS No. 620-23-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 620-23-5
Chemical Structure| 620-23-5
Chemical Structure| 620-23-5
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Product Citations

Product Citations

Shifali Shishodia ; Raymundo Nuñez ; Brayden P. Strohmier , et al. DOI: PubMed ID:

Abstract: PBRM1 is a subunit of the PBAF chromatin remodeling complex that uniquely contains six bromodomains. PBRM1 can operate as a tumor suppressor or tumor promoter. PBRM1 is a tumor promoter in prostate cancer, contributing to migratory and immunosuppressive phenotypes. Selective chemical probes targeting PBRM1 bromodomains are desired to elucidate the association between aberrant PBRM1 chromatin binding and cancer pathogenesis and the contributions of PBRM1 to immunotherapy. Previous PBRM1 inhibitors unselectively bind SMARCA2 and SMARCA4 bromodomains with nanomolar potency. We used our protein-detected NMR screening pipeline to screen 1968 fragments against the second PBRM1 bromodomain, identifying 17 hits with Kd values from 45 μM to >2 mM. Structure–activity relationship studies on the tightest-binding hit resulted in nanomolar inhibitors with selectivity for PBRM1 over SMARCA2 and SMARCA4. These chemical probes inhibit the association of full-length PBRM1 to acetylated histone peptides and selectively inhibit growth of a PBRM1-dependent prostate cancer cell line.

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 100-52-7 ; 123-11-5 ; 1711-06-4 ; 454-89-7 ; ; ; ; ; ; ; ; ; ; ; ; ; 118-92-3 ; 22458-07-7 ; ; ; ; ; 97-96-1 ; ; 89-98-5

Product Details of [ 620-23-5 ]

CAS No. :620-23-5 MDL No. :MFCD00003374
Formula : C8H8O Boiling Point : -
Linear Structure Formula :- InChI Key :OVWYEQOVUDKZNU-UHFFFAOYSA-N
M.W : 120.15 Pubchem ID :12105
Synonyms :
3-Methylbenzaldehyde
Chemical Name :3-Tolualdehyde

Calculated chemistry of [ 620-23-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.8
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 1.78
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.69 mg/ml ; 0.00574 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 1.4 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.249 mg/ml ; 0.00207 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 620-23-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 620-23-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 620-23-5 ]
  • Downstream synthetic route of [ 620-23-5 ]

[ 620-23-5 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 620-23-5 ]
  • [ 76074-47-0 ]
Reference: [1] Catalysis Letters, 2018, vol. 148, # 11, p. 3486 - 3491
  • 2
  • [ 620-23-5 ]
  • [ 1711-06-4 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 15, p. 3666 - 3669
[2] New Journal of Chemistry, 2017, vol. 41, # 3, p. 931 - 939
[3] Tetrahedron Letters, 2017, vol. 58, # 26, p. 2533 - 2536
  • 3
  • [ 620-23-5 ]
  • [ 2947-60-6 ]
Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 16, p. 2379 - 2384
  • 4
  • [ 620-23-5 ]
  • [ 1736-06-7 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 4, p. 658 - 660
  • 5
  • [ 90965-06-3 ]
  • [ 620-23-5 ]
  • [ 766-82-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 103, p. 59297 - 59301
  • 6
  • [ 141-82-2 ]
  • [ 620-23-5 ]
  • [ 68208-17-3 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 11, p. 1207 - 1212
[2] European Journal of Medicinal Chemistry, 1992, vol. 27, # 9, p. 961 - 965
[3] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
[4] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9152 - 9157
[5] Bulletin de la Societe Chimique de France, 1987, # 6, p. 1079 - 1083
[6] European Journal of Organic Chemistry, 2013, # 3, p. 557 - 565
[7] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1356 - 1365
  • 7
  • [ 141-82-2 ]
  • [ 620-23-5 ]
  • [ 3029-79-6 ]
  • [ 68208-17-3 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 37, p. 7449 - 7461
  • 8
  • [ 620-23-5 ]
  • [ 68208-17-3 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 1129,1133
  • 9
  • [ 620-23-5 ]
  • [ 5472-70-8 ]
Reference: [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1914, vol. 89, p. 106
  • 10
  • [ 74-89-5 ]
  • [ 620-23-5 ]
  • [ 39180-84-2 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: for 0.333333 h;
Stage #2: With sodium tetrahydroborate; water In methanol at 0 - 20℃;
Synthesis of m-tolylamine: To a solution of m-tolualdehyde (6.4 mL, 54.0 mmol) in MeOH (50 mL) was added 40percent aqueous methylamine (4.3 mL, 55.1 mmol). After 20 minutes, the mixture was cooled in an ice-bath, and sodium borohydride (3.07 g, 81.1 mmol) was added in small portions over 20 minutes. The mixture was then warmed to room temperature and stirred overnight. The reaction mixture was then concentrated under reduced pressure, and partitioned between water and CH2Cl2 (100 mL each). The aqueous layer was re-extracted with CH2Cl2 (2.x.50 mL), and the organic extracts were combined and washed with 2 N HCl (3.x.30 mL). The aqueous layer was washed with CH2Cl2 (50 mL), treated with concentrated NH4OH (until pH 12), and extracted with CH2Cl2 (3.x.100 mL). The organic extracts were combined, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give m-tolylamine (5.46 g, 75percent), which was used in Step D without further purification. 1H NMR (300 MHz, CDCl3) δ 7.26-7.05 (m, 4H), 3.72 (s, 2H), 2.46 (s, 3H), 2.35 (s, 3H).
Reference: [1] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 106-107
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 3798,3800
[3] Patent: US2862967, 1955, ,
  • 11
  • [ 620-23-5 ]
  • [ 39180-84-2 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 4, p. 600 - 603
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7219 - 7222
  • 12
  • [ 593-51-1 ]
  • [ 620-23-5 ]
  • [ 39180-84-2 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
  • 13
  • [ 620-23-5 ]
  • [ 82072-23-9 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 16, p. 1861 - 1865
  • 14
  • [ 620-23-5 ]
  • [ 1082041-78-8 ]
Reference: [1] Patent: WO2012/35078, 2012, A1,
[2] Patent: US2014/45872, 2014, A1,
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 789 - 801
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