42016-91-1

Basic information

• Product Name: 3,5-Diiodosalicyloyl chloride
• Synonyms: 3,5-DIIODOSALICYL CHLORIDE;2-hydroxy-3,5-diiodobenzoyl chloride;3,5-Diiodosalicyl;3,5-Diiodosalicyloyl chloride;BENZOYLCHLORIDE,2-HYDROXY-3,5-DIIODO;3,5-diiodo salicylic chloride
• CAS NO: 42016-91-1
• Molecular Formula: C₇H₃ClI₂O₂
• Molecular Weight: 408.36
• EINECS: 255-625-3
• Mol File: 42016-91-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 90 °C
• Boiling Point: 361.2 °C at 760 mmHg
• Flash Point: 172.2 °C
• Appearance: /
• Density: 2.578 g/cm³
• Vapor Pressure: 1.01E-05mmHg at 25°C
• Refractive Index: 1.744
• PKA: 5.17±0.48(Predicted)
• CAS DataBase Reference: 3,5-Diiodosalicyloyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Diiodosalicyloyl chloride(42016-91-1)
• EPA Substance Registry System: 3,5-Diiodosalicyloyl chloride(42016-91-1)

Safety Data

• Hazardous Substances Data: 42016-91-1(Hazardous Substances Data)

Usage

General Description

3,5-Diiodosalicyloyl chloride is a chemical compound with the molecular formula C13H6Cl2I2O3. It is a derivative of salicylic acid and has two iodine atoms attached to the 3 and 5 positions of the benzene ring, as well as a chloride group attached to the carboxyl group. 3,5-Diiodosalicyloyl chloride is commonly used in organic synthesis as a building block for the preparation of various biologically active compounds and pharmaceutical products. It is also used in the production of dyes, pigments, and other specialty chemicals. Additionally, 3,5-Diiodosalicyloyl chloride has been reported to exhibit antimicrobial and antifungal properties, making it potentially useful in medical and agricultural applications.

InChI:InChI=1/C7H3ClI2O2/c8-7(12)4-1-3(9)2-5(10)6(4)11/h1-2,11H

Upstream product

• 133-91-5 3,5-diiodosalicylic acid 

Downstream Products

• 42016-80-8 2-hydroxy-3,5-diiodo-benzoic acid-(3,4-dichloro-anilide) 
• 292637-51-5 C₁₄H₁₁I₂NO₂ 
• 14437-46-8 N-(4-Chlorophenyl)-2-hydroxy-3,5-diiodobenzamide 
• 290366-63-1 C₁₄H₁₁I₂NO₃ 
• 19503-64-1 2-hydroxy-3,5-diiodo-N-phenyl-benzamide 
• 79402-05-4 C₁₃H₈FI₂NO₂ 
• 14437-47-9 C₁₃H₈BrI₂NO₂ 
• 35735-82-1 2-hydroxy-3,5-diiodo-N-(4-phenoxyphenyl)benzamide 
• 1613336-77-8 N-(2-(1H-indol-3-yl)ethyl)-2-hydroxy-3,5-diiodobenzamide 
• 1613336-75-6 N-(4′-chloro-[1,1′-biphenyl]-4-yl)-2-hydroxy-3,5-diiodobenzamide 

Relevant articles and documents

Development of a novel probe for measuring drug binding to the F1*S variant of human alpha 1-acid glycoprotein

A novel probe was developed to measure drug association with the F1*S variant of the human serum protein alpha 1-acid glycoprotein (AGP). The molecule 2-hydroxy-3,5-diiodo-N-[2(diethylamino)ethyl]benzamide (DEDIC) binds to AGP, quenching its native fluorescence. This quenching was fitted to a two-site model giving apparent dissociation constants of 0.049 ± 0.005 and 12 ± 2 μM (mean ± SEM). Quenching of each of the separate variants of AGP by DEDIC was itself described by a two-site model, giving for the F1*S variant KD(F1*S)1 = 0.041 ± 0.010 μM and KD(F1*S)2 = 29 ± 7 μM; and for the A variant KD(A)1 = 0.31 ± 0.18 μM and KD(A)2 = 8.8 ± 0.7 μM. The utility of DEDIC in probing drug interactions with isolated variants was demonstrated in competition experiments with the model drugs amitriptyline and bupivacaine. In addition, the selectivity of DEDIC for variant F1*S rendered it capable of probing the binding of drugs (including the variant A-selective drug amitriptyline) to F1*S in a mixture of variants, such as occurs naturally in whole AGP. DEDIC is unique as an F1*S variant-selective probe of drug binding to whole AGP that is also sufficiently soluble to serve as a probe of drug binding to the lower affinity sites on isolated A and F1*S variants.

Iodinated 1,2-diacylhydrazines, benzohydrazide-hydrazones and their analogues as dual antimicrobial and cytotoxic agents

Hydrazide-hydrazones have been described as a scaffold with antimicrobial and cytotoxic activities as well as iodinated compounds. A resistance rate of bacterial and fungal pathogens has increased considerably. That is why we synthesized and screened twenty-two iodinated hydrazide-hydrazones 1 and 2, ten 1,2-diacylhydrazines 3 and their three reduced analogues 4 for their antibacterial, antifungal, and cytotoxic properties. Hydrazide-hydrazones were prepared by condensation of 4-substituted benzohydrazides with 2-/4-hydroxy-3,5-diiodobenzaldehydes, diacylhydrazines from identical benzohydrazides and 3,5-diiodosalicylic acid via its chloride. These compounds were investigated in vitro against eight bacterial and eight fungal strains. The derivatives were found potent antibacterial agents against Gram-positive cocci including methicillin-resistant Staphylococcus aureus with the lowest values of minimum inhibitory concentrations (MIC) of 7.81 μM. Four compounds inhibited also human pathogenic fungi (MIC of ≥1.95 μM). The derivatives had different degrees of cytotoxicity for HepG2 and HK-2 cell lines (IC50 values from 11.72 and 26.80 μM, respectively). Importantly, normal human cells exhibited lower sensitivity. The apoptotic effect was also investigated. In general, the presence of 3,5-diiodosalicylidene scaffold (compounds 1) is translated into enhanced both antimicrobial and cytotoxic properties whereas its 4-hydroxy isomers 2 share a low biological activity. N′-Benzoyl-2-hydroxy-3,5-diiodobenzohydrazides 3 have a non-homogeneous activity profile. Focusing on 4-substituted benzohydrazide part, the presence of an electron-withdrawing group (F, Cl, CF3, NO2) was found to be beneficial.

METHODS FOR TREATMENT OF CLOSTRIDIUM DIFFICILE INFECTIONS

In this study, we capitalized on the antimicrobial property and low oral bioavailability of known salicylanilide anthelmintics (closantel, rafoxanide, niclosamide, oxyclozanide) to target the gut pathogen. The anthelmintics displayed excellent potency against C. difficile strains 630 and 4118 (with MIC values as low as 0.06 - 0.13 μg/mL for rafoxanide) via a membrane depolarization mechanism, interestingly, closantel, rafoxanide and compound 8 were bactericidal against logarithmic- and stationary-phase cultures of the BI/NAP1/027 strain 4118. Further evaluation of the salicylanilides showed their preferential activity against Gram-positive over Gram-negative bacteria. Moreover, the salicylanilides were non-hemolytic and were non- toxic to mammalian cell lines HepG2 and HEK 293T/17 within the range of their in vitro MICs and MBCs. The salicylanilide anthelmintics exhibit desirable bactericidal and pharmacokinetic properties and are amenable to repositioning as anti-C. difficile agents.