22265-36-7

Basic information

• Product Name: 4-BROMO-BENZAMIDINE
• Synonyms: 4-BROMO-BENZAMIDINE;CHEMBRDG-BB 4012620;4-BROMOBENZENECARBOXIMIDAMIDE HYDROCHLORIDE;4-bromobenzammidine;4-bromobenzenecarboximidamide(SALTDATA: HCl);4-bromobenzenecarboximidamide 1HCl;4-BroMo-benzaMidine HCl salt;BenzenecarboxiMidaMide, 4-broMo-
• CAS NO: 22265-36-7
• Molecular Formula: C₇H₇BrN₂
• Molecular Weight: 199.05
• Product Categories: pharmacetical
• Mol File: 22265-36-7.mol

Chemical Properties

• Melting Point: 218℃
• Boiling Point: 261℃
• Flash Point: 112℃
• Appearance: /
• Density: 1.62
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.39±0.50(Predicted)
• CAS DataBase Reference: 4-BROMO-BENZAMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-BENZAMIDINE(22265-36-7)
• EPA Substance Registry System: 4-BROMO-BENZAMIDINE(22265-36-7)

Safety Data

• Hazardous Substances Data: 22265-36-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Bromo-benzamidine is used as a synthetic intermediate for the production of various chemical compounds. Its unique structure allows for the creation of a wide range of derivatives, making it a valuable component in the synthesis of new molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-Bromo-benzamidine is employed as a building block for the development of new drugs. Its structural features enable the design of potential therapeutic agents, contributing to the advancement of medicinal chemistry.
Used in Material Science:
4-Bromo-benzamidine is used as a component in the development of new materials with specific properties. Its integration into material compositions can lead to the creation of materials with tailored characteristics, such as improved stability or enhanced reactivity, for various applications in material science.
Used in Research and Development:
4-Bromo-benzamidine is utilized in research and development settings to explore its potential applications and properties. Its unique structure and reactivity make it an interesting subject for scientific investigation, potentially leading to new discoveries and innovations in various fields.

InChI:InChI=1/C7H7BrN2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H3,9,10)

Upstream product

• 55368-83-7 4-bromo-benzimidic acid ethyl ester hydrochloride 
• 19227-14-6 p-bromobenzamidoxime 
• 55368-42-8 4-bromobenzamidine hydrochloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 19402-64-3 ammonium benzenesulfonate 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 204588-96-5 2,4-Bis-(4-bromo-phenyl)-6-methyl-pyrimidine 
• 457613-56-8 2-(4-bromophenyl)-4,6-diphenylpyrimidine 
• 23449-08-3 2-(4-bromobenzenyl)-4,6-diphenyl-1,3,5-triazine 

Relevant articles and documents

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

Based on the novel allosteric site of deoxyhypusine synthase (DHPS), two series of 30 novel 5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-amine derivatives as DHPS inhibitors were designed and synthesized. Among them, compound8m, with the best DHPS inhibitory potency (IC50= 0.014 μM), exhibited excellent inhibition against melanoma cells, which was superior to that of GC7. Besides, molecular docking and molecular dynamics (MD) simulations further proved that compound8mwas tightly bound to the allosteric site of DHPS. Flow cytometric analysis and enzyme-linked immunosorbent assay (ELISA) showed that compound8mcould inhibit the intracellular reactive oxygen species (ROS) level. Furthermore, by western blot analysis, compound8meffectively activated caspase 3 and decreased the expressions of GP-100, tyrosinase, eIF5A2, MMP2, and MMP9. Moreover, both Transwell analysis and wound healing analysis showed that compound8mcould inhibit the invasion and migration of melanoma cells. In thein vivostudy, the tumor xenograft model showed that compound8meffectively inhibited melanoma development with low toxicity.

INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

Silver-catalyzed [3+2+1] annulation of aryl amidines with benzyl isocyanide

A silver-catalyzed [3+2+1] annulation of amidines with benzyl isocyanide toward 2,4-diaryl-1,3,5-triazines was developed. A variety of symmetrical and unsymmetrical products were obtained in moderate to good yields. This work also features an oxidant-free approach to 2,4-disubstituted triazines.

Preparation technique of dabigatran methanesulfonate

The invention discloses a preparation technique of dabigatran methanesulfonate. The technique comprises the following steps: 1) by using a compound I and glycine as raw materials, carrying out condensation and salification to obtain a compound II; 2) by using p-halobenzonitrile (III) as a raw material, synthesizing p-halobenzamidine (IV) under the actions of a catalyst and an aminating agent, and carrying out condensation on the p-halobenzamidine (IV) and n-hexyl chloroacetate to obtain a compound V; and 3) carrying out condensation and salification on the compound V and the compound II to obtain the dabigatran methanesulfonate. The synthesis method has the advantages of mild reaction conditions for each step and high selectivity, and is simple to operate. The dabigatran methanesulfonate has high yield and purity. The technique has the advantages of less discharge of three wastes and environment friendliness, does not need column chromatography purification, and is suitable for industrial production.

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.

AROMATIC HETEROCYCLIC COMPOUND

The compound represented by the general formula: wherein ring A is benzene which may be substituted and the like; ring B is benzene which may be substituted and the like; X is a single bond and the like; Y is alkyl which may be substituted and the like; Z is CR1 or nitrogen atom; R1 is hydrogen and the like; R2 is alkyl which may be substituted and the like or a pharmaceutically acceptable salt thereof is useful as a prevention/treatment agent of obesity, diabetes, and the like.

Electrochemical and mARC-catalyzed enzymatic reduction of para-substituted benzamidoximes: Consequences for the prodrug concept "amidoximes instead of amidines"

The mitochondrial amidoxime reducing component (mARC) activates amidoxime prodrugs by reduction to the corresponding amidine drugs. This study analyzes relationships between the chemical structure of the prodrug and its metabolic activation and compares its enzyme-mediated vs. electrochemical reduction. The enzyme kinetic parameters KM and Vmax for the N-reduction of ten para-substituted derivatives of the model compound benzamidoxime were determined by incubation with recombinant proteins and subcellular fractions from pig liver followed by quantification of the metabolites by HPLC. A clear influence of the substituents at position 4 on the chemical properties of the amidoxime function was confirmed by correlation analyses of 1H NMR chemical shifts and the redox potentials of the 4-substituted benzamidoximes with Hammett's σ. However, no clear relationship between the kinetic parameters for the enzymatic reduction and Hammett's σ or the lipophilicity could be found. It is thus concluded that these properties as well as the redox potential of the amidoxime can be largely ignored during the development of new amidoxime prodrugs, at least regarding prodrug activation.

Synthesis and structure-activity relationship of 4-amino-2-phenylpyrimidine derivatives as a series of novel GPR119 agonists

Through preparation and examination of a series of novel 4-amino-2-phenylpyrimidine derivatives as agonists for GPR119, we identified 2-(4-bromophenyl)-6-methyl-N-[2-(1-oxidopyridin-3-yl)ethyl]pyrimidin-4-amine (9t). Compound 9t improved glucose tolerance in mice following oral administration and showed good pharmacokinetic profiles in rats.

INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

Methods of treating pneumocystis carinii pneumonia

The present invention provides methods for treating Pneumocystis carinii pneumonia and Giardia lamblia in a subject in need of such treatment. The methods comprises administering to the subject a compound of Formula I: STR1 wherein: X and Y are located in