21304-38-1

Basic information

• Product Name: 1,2-BENZENEDIAMINE, 4-IODO-
• Synonyms: 1,2-BENZENEDIAMINE, 4-IODO-;4-Iodo-1,2-phenylenediamine97%;4-IODO-1,2-PHENYLENEDIAMINE 97%;1,2-Diamino-4-iodobenzene;2-Amino-5-iodoaniline;4-Iodo-1,2-benzenediamine;4-iodo-1,2-phenylenediaMine;2-Amino-4-iodoaniline
• CAS NO: 21304-38-1
• Molecular Formula: C₆H₇IN₂
• Molecular Weight: 234.03765
• Mol File: 21304-38-1.mol

Chemical Properties

• Melting Point: 73-77℃
• Boiling Point: 339 °C at 760 mmHg
• Flash Point: 158.8 °C
• Appearance: /Solid
• Density: 2.016
• Vapor Pressure: 9.46E-05mmHg at 25°C
• Refractive Index: 1.757
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 3.37±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: 1,2-BENZENEDIAMINE, 4-IODO-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BENZENEDIAMINE, 4-IODO-(21304-38-1)
• EPA Substance Registry System: 1,2-BENZENEDIAMINE, 4-IODO-(21304-38-1)

Safety Data

• HazardClass: 6.1
• Hazardous Substances Data: 21304-38-1(Hazardous Substances Data)

Usage

Uses

It is employed in the synthesis of N-(Benzimidazol-2-ylmethyl)iminodiacetic acids.

InChI:InChI=1/C6H7IN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2

Upstream product

• 20289-35-4 5-iodo-2-nitro-aniline 
• 20691-72-9 4-iodo-2-nitroaniline 
• 88-74-4 2-nitro-aniline 

Downstream Products

• 89219-01-2 N,N'-bis(chloroacetyl)-4-iodo-1,2-phenylenediamine 
• 645414-76-2 1-benzyl-6-phenyl-1H-benzoimidazole 
• 645414-77-3 1-benzyl-2-iodo-6-phenyl-1H-benzoimidazole 
• 645414-75-1 1-benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole 
• 645414-78-4 1,1'-dibenzyl-6-phenyl-1H,1'H-[2,5']bibenzoimidazolyl 
• 645414-79-5 1,1'-dibenzyl-2'-iodo-6-phenyl-1H,1'H-[2,5']bibenzoimidazolyl 
• 645414-80-8 1,1',1''-tribenzyl-6-phenyl-1H,1'H,1''H-[2,5';2',5'']terbenzoimidazole 
• 1116601-52-5 [(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 1116601-51-4 [(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 1116601-42-3 [(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 1116601-39-8 [(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 1192251-92-5 2-(2'-fluorobiphenyl-4-yl)-6-iodo-1H-benzimidazole 
• 1262317-43-0 (S)-2-{5-[2-((S)-1-benzyloxycarbonyl-piperidin-2-yl)-1H-benzoimidazol-5-ylethynyl]-1H-benzoimidazol-2-yl}-piperazine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester 
• 1262317-51-0 (S)-2-(5-{(E)-4-[2-((S)-1-benzyloxycarbonyl-piperidin-2-yl)-1H-benzoimidazol-5-yl]-but-1-en-3-ynyl}-1H-benzoimidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Synthesis and Biological Evaluation of Novel 2-Aryl Benzimidazoles as Chemotherapeutic Agents

Here, we describe the synthesis and preliminary biological evaluation of novel N-unsubstituted and N-methylated 2-aryl benzimidazole derivatives that contain fluorinated or hydroxylated alkyl substituents in the 4-N-aryl position and different substitution patterns (H vs Br vs I) in the benzimidazole ring. For the selected compounds and for comparison purposes, the congener benzothiazoles were also tested. The cytotoxic effect of 11 benzazole derivatives was evaluated in a panel of human cancer cell lines, such as breast (MCF7), melanoma (A375), cervix (HeLa), and glioblastoma (U87). In general, the compounds exerted a moderate cytotoxic activity against all cells tested. In particular, for the A375 and HeLa cells, the N-unsubstituted benzimidazoles 2 and 3 displayed a better cytotoxic profile than the respective N-methylated benzimidazole congeners (5 and 7). The biodistribution of compound 2, which has shown the highest cytotoxic activity active in the U87 glioblastoma cells (IC50= 45.2 ± 13.0), was evaluated in CD1 mice using its18F-labeled counterpart ([18F]2). These studies showed that compound 2 can cross the blood brain barrier with a reasonable brain uptake (1.24 and 2.81%I.A./g at 5 and 60 min p.i., respectively), which is a crucial issue for systemic chemotherapy of glioblastoma. Altogether, the in vitro antitumoral activity of benzimidazole 2 against the U87 cells and the ability of its18F-congener to cross the blood brain barrier provide a strong rationale to consider the reported fluoroalkylated 2-aryl benzimidazoles as lead candidates for the generation of chemotherapeutic agents, in particular, against highly aggressive brain tumors such as glioblastoma.

RADIOACTIVE IODINE LABELED STYRYL SUBSTITUTED AROMATIC HETEROCYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide a novel tau protein imaging agent that allows imaging of biological tau protein by a noninvasive, nuclear medical method. SOLUTION: The present invention provides a radioactive iodine labeled styryl substituted aromatic heterocyclic compound represented by a predetermined general formula or a salt thereof, or a radioactive medicine comprising the same. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Exploring the Strength of the H-Bond in Synthetic Models for Heme Proteins: The Importance of the N?H Acidity of the Distal Base

The distal hydrogen bond (H-bond) in dioxygen-binding proteins is crucial for the discrimination of O2with respect to CO or NO. We report the preparation and characterization of a series of ZnIIporphyrins, with one of three meso-phenyl rings bearing both an alkyl-tethered proximal imidazole ligand and a heterocyclic distal H-bond donor connected by a rigid acetylene spacer. Previously, we had validated the corresponding CoIIcomplexes as synthetic model systems for dioxygen-binding heme proteins and demonstrated the structural requirements for proper distal H-bonding to CoII-bound dioxygen. Here, we systematically vary the H-bond donor ability of the distal heterocycles, as predicted based on pKavalues. The H-bond in the dioxygen adducts of the CoIIporphyrins was directly measured by Q-band Davies-ENDOR spectroscopy. It was shown that the strength of the hyperfine coupling between the dioxygen radical and the distal H-atom increases with enhanced acidity of the H-bond donor.

Structure-Activity Relationship Study of Heterocyclic Phenylethenyl and Pyridinylethenyl Derivatives as Tau-Imaging Agents That Selectively Detect Neurofibrillary Tangles in Alzheimers Disease Brains

In order to explore novel tau-imaging agents that can selectively detect neurofibrillary tangles in Alzheimers disease (AD) brains, we designed and synthesized a series of heterocyclic phenylethenyl and (3-pyridinyl)ethenyl derivatives with or without a dimethyl amino group. In in vitro autoradiography using AD brain sections, all radioiodinated ligands with a dimethyl amino group bound to Aβ deposits in the sections. In contrast, the ligands without a dimethyl amino group showed different patterns of radioactivity accumulation in the sections depending on the kind of heterocycle contained in their molecules. Particularly, a phenylethenyl benzimidazole derivative ([125I]64) showed marked radioactivity accumulation in the temporal lobe which corresponded with the distribution of tau deposits. [125I]64 also showed the most favorable pharmacokinetics in normal mouse brains (3.69 and 0.06% ID/g at 2 and 60 min postinjection, respectively) among all ligands in this study. Taken together, these results suggest that [123I]64 may be a new candidate tau-imaging agent.

Synthesis and biological evaluation of 5-substituted derivatives of benzimidazole

A series of eight novel 5-substituted derivatives of benzimidazole was synthesized by condensation of the corresponding diamine with ethyl 4-[4- -(2-chlorophenyl)piperazin-1-yl]butanoate in refluxing 4 M hydrochloric acid. In vitro antibacterial activity against ten strains, namely Bacillus subtilis, Clostridium sporogenes, Streptosporangium longisporum, Micrococcus flavus, Sarcina lutea, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis and Proteus vulgaris and antifungal activity against two fungal strains, namely Candida albicans and Saccharomyces cerevisiae, were evaluated. Of all the compounds screened for activity, 2-{3-[4-(2-chlorophenyl) piperazin-1-yl]propyl}-5-iodo-1H-benzimidazole and 2-{3-[4-(2-chlorophenyl) piperazin-1-yl]propyl}-5-methyl-1H-benzimidazole were associated with higher antifungal activity than commercial drugs.

Inhibition and Dispersion of Bacterial Biofilms with 2-Aminobenzimidazole Derivatives

Compounds described herein inhibit biofilm formation or disperse pre-formed biofilms of Gram-negative bacteria. Biofilm-inhibitory compounds can be encapsulated or contained in a polymer matrix for controlled release. Coatings, films, multilayer films, hydrogels, microspheres and nanospheres as well as pharmaceutical compositions and disinfecting compositions containing biofilm-inhibitory compounds are also provided. Methods for inhibiting formation of biofilms or dispersing already formed biofilms are provided. Methods for treating infections of gram-negative bacteria which form biofilms, particularly those of Pseudomonas and more particularly P. aeruginosa.

ALLOSTERIC PROTEIN KINASE MODULATORS

The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

2-aminobenzimidazole derivatives strongly inhibit and disperse Pseudomonas aeruginosa biofilms

Bacterial biofilms are exceptionally difficult to clear using traditional antibiotics and constitute a significant health threat. 2-Aminobenzimidazole derivatives (see scheme) are capable of strongly inhibiting the growth of and dispersing Pseudomonas aeruginosa biofilms. These molecules were found to modulate quorum sensing in reporter strains, and represent some of strongest P. aeruginosa biofilm inhibitors known. Copyright

4-benzimidazolyl-3-phenylbutanoic acids as novel pif-pocket-targeting allosteric inhibitors of protein kinase PKCΧ

Protein kinase inhibitors with an allosteric mode of action are expected to reach, in many cases, higher selectivity for the target enzyme than ATP-competitive compounds. Therefore, basic research is aiming at identifying and establishing novel sites on the catalytic domain of protein kinases which might be targeted by allosteric inhibitors. We previously published the first structure-activity relationships (SARs) for allosteric activators of protein kinase PDK1. Here, we present the design, synthesis, and SAR data on a series of novel compounds, 4-benzimidazolyl-3-phenylbutanoic acids, that inhibit the atypical protein kinace C (PKC) Χ via binding to the PIF-pocket. Key positions were identified in the compounds that can be modified to increase potency and selectivity. Some congeners showed a high selectivity toward PKCΧ, lacking inhibition of the most closely related isoform, PKC1, and of further AGC kinases. Furthermore, evidence is provided that these compounds are also active toward cellular PKCΧ without loss of potency compared to the cell-free assay.

INHIBITORS OF HCV NS5A

Provided herein are compounds, pharmaceutical compositions and combination therapies for inhibition of hepatitis C.