4-iodo-3-nitrobenzamide Chemical Properties

Melting point:

150-153°

Boiling point:

344.8±32.0 °C(Predicted)

Density 

2.055±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO: soluble5mg/mL, clear

form 

powder

pka

14?+-.0.50(Predicted)

color 

white to beige

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

26

WGK Germany 

3

HS Code 

2921490090

4-iodo-3-nitrobenzamide Usage And Synthesis

Description

Iniparib (160003-66-7) was originally thought to be a PARP1 inhibitor but this is controversial.1,2?Inhibits ionizing radiation-induced single-stranded DNA break repair in lymphoid cell lines?in vivo.3?Inhibits growth of certain breast cancer cell lines?in vitro. Iniparib non-selectively modifies cysteine-containing proteins in tumor cells.4

Uses

Iniparib is an irreversible PARP1 inhibitor. Studies show that potential therapeutic agent for the treatment of cancer, including triple-negative breast cancer.

Uses

Iniparib (BSI-201) is an antineoplastic originally thought to be a poly(ADP-ribose) polymerase-1 (PARP-1) inhibitor. Recent studies indicate Iniparib is not a PARP-1 inhibitor, and its mechanism of action is currently unknown.

Uses

Poly(ADP-ribose) polymerase (PARP) is a critical DNA repair enzyme involved in DNA single-strand break repair via the base excision repair pathway. PARP1 is activated by DNA damage. Inhibiting its activity has been linked to synthetic lethality and loss of either of the breast cancer susceptibility genes, BRCA1 and BRCA2. BSI-201 is an irreversible, noncompetitive inhibitor of PARP1 that disrupts binding between PARP1 and DNA by interacting with the DNA binding domain. It produces rapid apoptosis in various cancer cell lines with IC50 values ranging from 40-128 μM and is not toxic in Syrian hamsters at doses as high as 200 mg/kg. In phase II clinical studies, BSI-201, in combination with carboplatin and gemcitabine, has produced promising results in "triple-negative" breast cancers, increasing median overall survival from 7.7 months to 12.3 months.

Definition

ChEBI: 4-iodo-3-nitrobenzamide is a carbonyl compound and an organohalogen compound.

Synthesis

General procedure for the synthesis of 3-nitro-4-iodobenzamide from methyl 4-iodo-3-nitrobenzoate: 3.7 g of methyl 4-iodo-3-nitrobenzoate was dissolved in 30 mL of methanol and transferred to a reaction flask. The reaction mixture was stirred at a constant temperature of 35°C while ammonia was passed through. The reaction process was monitored by thin layer chromatography (TLC) with the unfolding agent ratio of ethyl acetate:petroleum ether=1:1 (v/v). After the reaction was complete, the reaction mixture was concentrated to dryness under reduced pressure to give 3.3 g of yellow solid crude product. The crude product was recrystallized with 19.8 mL of ethanol, followed by filtration to give yellow crystals. The crystals were dried under vacuum to finally obtain 3.0 g of 3-nitro-4-iodobenzamide, which was analyzed by high performance liquid chromatography (HPLC) with 99.75% purity and 85.2% yield.

IC 50

PARP1

References

[1] SINHA G. Downfall of iniparib: a PARP inhibitor that doesn’t inhibit PARP after all.[J]. JNCI Journal of the National Cancer Institute, 2014, 106 1: djt447. DOI:10.1093/jnci/djt447
[2] JOAQUIN MATEO. Appraising iniparib, the PARP inhibitor that never was—what must we learn?[J]. Nature Reviews Clinical Oncology, 2013, 10 12: 688-696. DOI:10.1038/nrclinonc.2013.177
[3] WENJIAN MA. Differential effects of poly(ADP-ribose) polymerase inhibition on DNA break repair in human cells are revealed with Epstein-Barr virus.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2012, 109 17: 6590-6595. DOI:10.1073/pnas.1118078109
[4] XUESONG LIU. Iniparib nonselectively modifies cysteine-containing proteins in tumor cells and is not a bona fide PARP inhibitor.[J]. Clinical Cancer Research, 2012, 18 2: 510-523. DOI:10.1158/1078-0432.ccr-11-1973

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