BMH21 Chemical Properties

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: soluble1mg/mL, clear (warmed)

pka

7.90±0.20(Predicted)

form 

powder

color 

light yellow to dark yellow

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

BMH21 Usage And Synthesis

Uses

BMH-21 has been used in cell culture.

General Description

BMH-21 is a planar heterocyclic small molecule DNA intercalator.

Biochem/physiol Actions

BMH-21 is a potent inhibitor of RNA Pol I. BMH-21 binds strongly to GC-rich DNA sequences, ultimately inhibiting RNA Pol I, blocking transcription and disrupting the nucleolar structure. BMH-1 causes dissociation of the RPA194 catalytic subunit from Pol I, and disassembly of Pol I:DNA complexes. The compound BMH-21 inhibits proliferation of a broad range of tumor cell lines.

Synthesis

Method A: Synthesis of amide analogs (4). Synthesis of N-[2-(dimethylamino)ethyl]-12-oxo-12H-benzo[g]pyrido[2,1-b]quinazoline-4-carboxamide. 12-Oxo-12H-benzo[g]pyrido[2,1-b]quinazoline-4-carboxylic acid (50 mg, 0.17 mmol) and TBTU (82.9 mg, 0.26 mmol) were dissolved in DMF (1 mL) and DbEA (90 μL, 0.52 mmol) was added. After stirring for 15 min at room temperature, N,N-dimethylethylenediamine (28.4 μL, 0.26 mmol) was added and stirring was continued for 16 hours. The reaction mixture was poured into 100 mL of cold water with stirring, and the solid was collected by filtration and dried under vacuum to afford the target product N-[2-(dimethylamino)ethyl]-12-oxo-12H-benzo[g]pyrido[2,1-b]quinazoline-4-carboxamide (36 mg, 0.10 mmol, 58.0% yield) as a yellow solid.1H NMR (400 MHz , DMSO-d6) δ ppm 11.50 (br.s, 1H), 9.10 (s, 1H), 8.91 (d, J=5.81 Hz, 1H), 8.55 (d, J=5.56 Hz, 1H), 8.28-8.34 (m, 2H), 8.12 (d, J=8.34 Hz, 1H), 7.73 (t, J=7.45 Hz , 1H), 7.61 (t, J=7.33 Hz, 1H), 7.05 (t, J=7.07 Hz, 1H), 3.56 (d, J=5.05 Hz, 2H), 2.59 (t, J=5.94 Hz, 2H), 2.40 (s, 6H).1H NMR (400 MHz, CDCl3) δ ppm 11.70 (br.s. 1H), 9.10 (s, 1H), 8.94 (dd, J=7.33,1.77 Hz, 1H), 8.73 (dd, J=6.82,1.77 Hz, 1H), 8.29 (s, 1H), 8.12 (d, J=8.59 Hz, 1H), 8.00 (d, J=8.34 Hz, 1H), 7.66 (t, J= 7.58 Hz, 1H), 7.52-7.60 (m, 1H), 6.89 (t, J=7.07 Hz, 1H), 3.66-3.77 (m, 2H), 2.71 (t, J=6.06 Hz, 2H), 2.49 (s, 6H). ms [M+1]=361.

in vivo

storage

Store at -20°C

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4950 - 4961
[2] Patent: WO2015/143293, 2015, A1. Location in patent: Paragraph 0084

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