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

4-iodo-3-nitrobenzamide is an organic compound with the molecular formula C7H4I2NO4. It is characterized by the presence of an iodine atom at the 4th position and a nitro group at the 3rd position on a benzene ring, with an amide functional group attached. 4-iodo-3-nitrobenzamide has potential applications in various fields due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
4-iodo-3-nitrobenzamide is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Cancer Treatment:
4-iodo-3-nitrobenzamide is used as a potential therapeutic agent for the treatment of cancer, including triple-negative breast cancer. It has been shown to inhibit ionizing radiation-induced single-stranded DNA break repair in lymphoid cell lines in vivo and to inhibit the growth of certain breast cancer cell lines in vitro.
Used in Antineoplastic Drug Development:
4-iodo-3-nitrobenzamide is used as an antineoplastic agent, originally thought to be a poly(ADP-ribose) polymerase-1 (PARP-1) inhibitor. Recent studies indicate that its mechanism of action is currently unknown, but it has shown potential in disrupting the binding between PARP1 and DNA, leading to rapid apoptosis in various cancer cell lines.
Used in DNA Repair Inhibition:
4-iodo-3-nitrobenzamide is used to inhibit the activity of poly(ADP-ribose) polymerase (PARP), a critical DNA repair enzyme involved in DNA single-strand break repair via the base excision repair pathway. Inhibiting PARP1 activity has been linked to synthetic lethality and loss of either of the breast cancer susceptibility genes, BRCA1 and BRCA2, making it a potential target for cancer treatment.
Used in Drug Delivery Systems:
To enhance the applications and efficacy of 4-iodo-3-nitrobenzamide against cancer cells, novel drug delivery systems have been developed. Various organic and metallic nanoparticles have been employed as carriers for 4-iodo-3-nitrobenzamide delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

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

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

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.