63450-84-0

Usage

Uses

Used in Medical Procedures:
Methyl 4-aminobenzoate hydrochloride is used as a local anesthetic agent for [providing temporary loss of sensation in targeted areas] during [dental work, minor surgeries, and dermatological treatments]. Its rapid onset of action and low systemic toxicity make it a preferred choice for such procedures.
Used in Veterinary Medicine:
In the veterinary field, Methyl 4-aminobenzoate hydrochloride is used as a local anesthetic for [blocking nerve signals and inducing temporary insensitivity] in animals during [medical and surgical interventions], similar to its application in human medicine.

InChI:InChI=1/C8H9NO2.ClH/c1-11-8(10)6-2-4-7(9)5-3-6;/h2-5H,9H2,1H3;1H

Upstream product

• 619-50-1 4-nitrobenzoic acid methyl ester 
• 17012-22-5 methyl 4-acetamidobenzoate 
• 82525-64-2 chloro-N-(4-methoxycarbonylphenyl)acetamide 
• 619-45-4 4-methoxycarbonyl aniline 
• 150-13-0 4-amino-benzoic acid 
• 75-36-5 acetyl chloride 
• 67-56-1 methanol 

Downstream Products

• 108583-15-9 methyl 4-(1H-indol-3-ylmethyleneimino)-benzoate 
• 174740-33-1 4-{8-[((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Acetoxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-octanoylamino}-benzoic acid methyl ester 
• 108583-16-0 4-(1H-indol-3-yl-methyleneimino)benzoic acid hydrazide 
• 108583-12-6 4-(1H-indol-3-ylmethyleneimino)benzoic acid benzylidenehydrazide 
• 108583-13-7 4-{[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-amino}-benzoic acid [1-phenyl-eth-(Z)-ylidene]-hydrazide 
• 108583-09-1 4-(1H-indol-3-ylmethyleneimino)benzoic acid 3-chloro-benzylidenehydrazide 
• 108583-11-5 4-(1H-indol-3-ylmethyleneimino)benzoic acid 4-methoxy-benzylidenehydrazide 
• 108583-08-0 4-(1H-indol-3-ylmethyleneimino)benzoic acid 2-hydroxy-benzylidenehydrazide 
• 108583-10-4 4-(1H-indol-3-ylmethyleneimino)benzoic acid 2-methoxy-benzylidenehydrazide 
• 108583-14-8 4-(1H-indol-3-ylmethyleneimino)benzoic acid 3-methoxy-4-hydroxy-benzylidenehydrazide 
• 129673-10-5 (S)-4-[[(3-acetylthio)-2-methyl-1-oxopropyl]amino]benzoic acid, methyl ester 
• 1446014-99-8 (S)-methyl 4-(2-((tert-butoxycarbonyl)amino)-2-phenylacetamido)benzoate 
• 1587675-53-3 (S)-methyl 4-(2-(2-naphthamido)-2-phenylacetamido)benzoate 
• 1587675-56-6 (S)-methyl 4-(2-(4-fluorobenzamido)-2-phenylacetamido)benzoate 

Relevant academic research and scientific papers

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

Discovery of indole-3-butyric acid derivatives as potent histone deacetylase inhibitors

In discovery of HDAC inhibitors (HDACIs) with improved anticancer potency, structural modification was performed on the previous derived indole-3-butyric acid derivative. Among all the synthesised compounds, molecule I13 exhibited high HDAC inhibitory and antiproliferative potencies in the in?vitro investigations. The IC50 values of I13 against HDAC1, HDAC3, and HDAC6 were 13.9, 12.1, and 7.71 nM, respectively. In the cancer cell based screening, molecule I13 showed increased antiproliferative activities in the inhibition of U937, U266, HepG2, A2780, and PNAC-1 cells compared with SAHA. In the HepG2 xenograft model, 50 mg/kg/d of I13 could inhibit tumour growth in athymic mice compared with 100 mg/kg/d of SAHA. Induction of apoptosis was revealed to play an important role in the anticancer potency of molecule I13. Collectively, a HDACI (I13) with high anticancer activity was discovered which can be utilised as a lead compound for further HDACI design.

Discovery of N-(2-Amino-4-Fluorophenyl)-4-[bis-(2-Chloroethyl)-Amino]-Benzamide as a Potent HDAC3 Inhibitor

In discovery of HDAC inhibitors with improved activity and selectivity, fluorine substitution was performed on our previously derived lead compound. The synthesized molecules N-(2-amino-4-fluorophenyl)-4-[bis-(2-chloroethyl)-amino]-benzamide (FNA) exhibited class I (HDAC1, 2, and 3) selectivity in the in vitro enzymatic assay and especially potent against HDAC3 activity (IC50: 95.48 nM). The results of in vitro antiproliferative assay indicated that FNA exhibited solid tumor cell inhibitory activities with IC50 value of 1.30 μM against HepG2 cells compared with SAHA (17.25 μM). Moreover, the in vivo xenograft model study revealed that FNA could inhibit tumor growth with tumor growth inhibition (TGI) of 48.89% compared with SAHA (TGI of 48.13%). Further HepG2 cell–based apoptosis and cell cycle studies showed that promotion of apoptosis and G2/M phase arrest make contributions to the antitumor activity of FNA. In addition, drug combination results showed that 0.5 μM of FNA could improve the anticancer activity of taxol and camptothecin. The present studies revealed the potential of FNA utilized as a high potent lead compound for further discovery of isoform selective HDAC inhibitors.

HDAC INHIBITORS AND USES THEREOF

The present invention relates to histone deacetylase inhibitors, and to pharmaceutical compositions comprising the compounds, useful for the treatment of ischemia-reperfusion injury and for cardioprotection.

Discovery of N-(2-aminophenyl)-4-(bis(2-chloroethyl)amino)benzamide as a potent histone deacetylase inhibitor

Inhibition of histone deacetylases (HDACs) has been an important emerging therapy for the treatment of multiple cancers. However, the application of HDAC inhibitors is restricted by the limited potency against solid tumors. In order to discover novel HDAC inhibitors with potent antitumor activities, nitrogen mustard group was introduced to the structure of CI994. The derived molecule N-(2-aminophenyl)-4-(bis(2-chloroethyl)amino) benzamide (NA) exhibited enzyme inhibitory pattern of class I selectivity with IC50 values of 95.2, 260.7, and 255.7 nM against HDAC1, HDAC2, and HDAC3, respectively. In the antiproliferative assay, NA exhibited 10.3-fold (2.66 μM) and 11.3-fold (1.73 μM) higher potency than did suberoylanilide hydroxamic acid (SAHA) (27.3 and 19.5 μM) in inhibition of A2780 and HepG2 cell growth, respectively. Further HepG2 cell-based cell cycle and apoptosis studies revealed that induction of the G2/M phase arrest and cell apoptosis contributes to the antitumor effects of NA. It is suggested that NA could be utilized as a lead compound in the development of bifunctional HDAC inhibitors for the treatment of solid tumors.

Aryl nitrogen mustard type histone deacetylation enzyme inhibitor as well as preparation method thereof and application thereof

The invention discloses a powerful histone deacetylation enzyme inhibitor, relates to a compound with a structure as shown in formula I, various optical isomers thereof, a medically acceptable salt and a solvent compound. The invention further relates to a pharmaceutical composition comprising the compound with the structure as shown in formula I and the pharmaceutical purpose thereof. The powerful histone deacetylation enzyme inhibitor can effectively treat a disease with histone deacetylation enzyme activity abnormal expression. The formula is shown in the description.

Fluorescent-labeled amino acid as well as preparation method and application thereof

The invention discloses a fluorescent-labeled amino acid. The fluorescent-labeled amino acid has the structure shown in a formula I: (the formula is shown in the description); stable covalent bondingis formed between an amino acid molecule and a fluorescence dye molecule; the fluorescent-labeled amino acid has high stability and high biocompatibility in the detection environments such as serum, and is suitable for detection of biological molecules such as protein and polypeptide inside and outside cells. Because the strokes shift of the fluorescence dye molecule is large, the fluorescent-labeled amino acid has the advantages of high fluorescence stability, high fluorescence quantum yield and high imaging result signal-to-noise ratio. The invention discloses a preparation method of the fluorescent-labeled amino acid. The preparation method is mild in reaction condition, simple to operate and high in reaction selectivity; the high-yield fluorescent-labeled amino acid can be prepared.

Histone deacetylase inhibitor N-(2'-aminophenyl)-4-(bis(2-chloroethyl)amino)benzamide, preparation method and application thereof

Belonging to the technical field of medicinal chemistry, the invention in particular relates to a histone deacetylase inhibitor, a preparation method and application thereof. The invention provides a potent histone deacetylase inhibitor, the invention relates to a compound with a structural formula (I), and also relates to cis-trans isomers thereof, pharmaceutically acceptable salts, solvates and prodrugs. The invention also relates to a pharmaceutical composition containing the compound shown as structural formula (I) and pharmaceutical use thereof. The histone deacetylase inhibitor provided by the invention can effectively treat histone deacetylase activity abnormally expressed diseases.

Development of N-hydroxybenzamide derivatives with indole-containing cap group as histone deacetylases inhibitors

Histone deacetylases inhibitors (HDACIs) have captured more and more attention in many diseases therapies, of which cancer is the most intractable. A novel series of N-hydroxybenzamide derivatives containing indole cap group was designed and synthesized. Most compounds exhibited excellent HDACs inhibitory activity, especially 8q-8v with low nanomolar IC50 values (1.5-13.0 nM), which were much more potent than the positive control SAHA. The most potent compound 8r showed slightly higher growth inhibitory activity than SAHA in multiple tumor cell lines, even though, antiproliferative activity of 8r seemed inferior to its HDAC inhibition activity. Poor transcellular permeability obtained from the result of HDAC class I cellular assay could explain the inferior antiproliferative activity. In addition, 8r displayed similar HDAC IIa cellular activity to class I, which indicated 8r might be a potent pan-HDAC inhibitor.