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Chemical Structure| 1885-31-0 Chemical Structure| 1885-31-0

Structure of 1885-31-0

Chemical Structure| 1885-31-0

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Product Citations

Shifali Shishodia ; Raymundo Nuñez ; Brayden P. Strohmier ; Karina L. Bursch ; Christopher J. Goetz ; Michael D. Olp , et al.

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.

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Product Details of [ 1885-31-0 ]

CAS No. :1885-31-0
Formula : C8H10N2O
M.W : 150.18
SMILES Code : O=C(N)C1=C(C)C=CC=C1N
MDL No. :MFCD09729171
InChI Key :IYKKLCLIASEVDG-UHFFFAOYSA-N
Pubchem ID :16782469

Safety of [ 1885-31-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H315-H319-H332-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1885-31-0 ]

* 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.

  • Downstream synthetic route of [ 1885-31-0 ]

[ 1885-31-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 42926-52-3 ]
  • [ 1885-31-0 ]
  • 2-(2-ethoxybenzamido)-6-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; In dichioromethane; Preparation 5 2-(2-Ethoxybenzamido)-6-methylbenzamide A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), <strong>[42926-52-3]2-ethoxybenzoyl chloride</strong> (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichioromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichioromethane (2*100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3*100 ml) and brine (100 ml), then dried (Na2SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colourless solid (6.86g, 63%), m.p. 166-168 C.
With pyridine; In dichloromethane; PREPARATION 5 2-(2-Ethoxybenzamido)-6-methylbenzamide A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), <strong>[42926-52-3]2-ethoxybenzoyl chloride</strong> (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichloromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichloromethane (2*100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3*100 ml) and brine (100 ml), then dried (Na2 SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colorless solid (6.86 g, 63%), m.p. 166-168 C. Found: C,68.28; H,5.97; N,9.42. C17 H18 N2 O3 requires C;68.44; H,6.08; N,9.39%.
 

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