160003-66-7

Basic information

• Product Name: 4-iodo-3-nitrobenzamide
• Synonyms: 4-iodo-3-nitrobenzamide;Iniparib;BSI-201;IND-71677;NSC-746045;BSI-201 (Iniparib);Iniparib (BSI-201);iniparib/NSC-746045
• CAS NO: 160003-66-7
• Molecular Formula: C₇H₅IN₂O₃
• Molecular Weight: 292.03
• EINECS: 1308068-626-2
• Product Categories: Inhibitor;Antineoplastic;Inhibitors
• Mol File: 160003-66-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 344.754 °C at 760 mmHg
• Flash Point: 162.302 °C
• Appearance: white to beige/
• Density: 2.056 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: room temp
• Solubility: DMSO: soluble5mg/mL, clear
• PKA: 14?+-.0.50(Predicted)
• 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.
• CAS DataBase Reference: 4-iodo-3-nitrobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-iodo-3-nitrobenzamide(160003-66-7)
• EPA Substance Registry System: 4-iodo-3-nitrobenzamide(160003-66-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 160003-66-7(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 160003-66-7 differently. You can refer to the following data:
1. Iniparib is an irreversible PARP1 inhibitor. Studies show that potential therapeutic agent for the treatment of cancer, including triple-negative breast cancer.
2. 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.
3. 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.

References

1) Sinha?et al. (2014),?Downfall of iniparib: a PARP inhibitor that doesn’t inhibit PARP after all; J. Natl. Cancer Inst.,?106?447 2) Mateo?et al.?(2013),?Appraising iniparib, the PARP inhibitor that never was –what must we learn?;?Nat. Rev. Clin. Oncol.,?10?688 3) Ma?et al. (2012),?Differential effects of poly(ADP-ribose) polymerase inhibition on DNA break repair in human cells are revealed with Epstein-Barr virus; Proc. Natl. Acad. Sci. USA,?109?6590 4) Liu?et al. (2012),?Iniparib nonselectively modifies cysteine-containing proteins in tumor cells and is not a bona fide PARP inhibitor; Clin. Cancer Res.,?18?510

InChI:InChI=1/C7H5IN2O3/c8-5-2-1-4(7(9)11)3-6(5)10(12)13/h1-3H,(H2,9,11)

Upstream product

• 532406-56-7 4-iodo-3-nitrobenzoyl chloride 
• 27329-27-7 4-methyl-2-nitrobenzoic acid 
• 5326-39-6 4-iodo-3-nitrotoluene 
• 879-93-6 4-bromo-3-nitrobenzamide 
• 1336-21-6 ammonium hydroxide 
• 35674-27-2 4-iodo-3-nitrobenzoic acid 

Relevant articles and documents

Nickel-catalysed aromatic Finkelstein reaction of aryl and heteroaryl bromides

A fast and efficient nickel-catalysed iodination reaction of aryl and heteroaryl bromides has been developed. The transformation was found to be general for a wide range of substrates and was used for the synthesis of iodo-PK11195, an imaging agent of Alzheimer's disease and iniparib, a compound used in the treatment of breast cancer.

PROCESS FOR THE PREPARATION OF 4-IODO-3-NITROBENZAMIDE

A process for the preparation of 4-iodo-3-nitrobenzamide free from the impurities formed due to nucleophilic substitution of the labile iodo group is disclosed.

Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. Can an "Inverted Built-in Solvation" Be Responsible for the Peculiar Activation by an o-Carboxamido Group in SNAr Reactions with an Anionic Nucleophile?

A kinetic study of the title reactions has allowed an interpretation of the higher efficiency of an o-carboxamido group with respect to an o-carbomethoxy group in activating the benzenethiolate-dehalogenation reactions in methanol (kCONH2/kCO2Me 2.2-3.0) as due to an interaction between the anionic nucleophile and the hydrogen atoms of the carboxamido group. An inversion of the activating power of the two groups (kCONH2/kCO2Me 0.14) in the reactions with the same nucleophile has been observed when they are in a para-position. Moreover, for piperidino-dehalogenation reactions in methanol kCONH2/kCO2Me ratios less than unity (0.2-0.6) have been observed independently of the position (ortho or para) of the carboxamido and carbomethoxy groups with respect to the reaction center.