66493-39-8

Usage

Uses

Used in Pharmaceutical Industry:
BOC-4-ABZ-OH is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to protect the amino group during chemical reactions. The BOC protecting group can be selectively removed under mild acidic conditions, enabling the formation of desired amide or peptide bonds in the final product.
Used in Chemical Synthesis:
In the field of chemical synthesis, BOC-4-ABZ-OH serves as a versatile building block for the creation of complex organic molecules. Its protected amino group allows for selective reactions at other functional groups present in the molecule, facilitating the synthesis of target compounds with specific properties and applications.
Used in Research and Development:
BOC-4-ABZ-OH is utilized in research and development for the study of B complex factors and their role in various biological processes. Its protected structure allows for the investigation of the effects of different protecting groups on the reactivity and properties of aminobenzoic acid derivatives, contributing to the advancement of scientific knowledge in this area.

InChI:InChI=1/C12H15NO4/c1-12(2,3)17-11(16)13-9-6-4-8(5-7-9)10(14)15/h4-7H,1-3H3,(H,13,16)(H,14,15)/p-1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 150-13-0 4-amino-benzoic acid 
• 124-38-9 carbon dioxide 
• 131818-17-2 tert-butyl (4-bromophenyl)carbamate 
• 97364-15-3 4-(1-hydroxyethyl)benzoic acid 
• 201230-82-2 carbon monoxide 
• 159217-89-7 N-Boc-4-iodoaniline 
• 94-09-7 p-aminoethylbenzoate 
• 619-45-4 4-methoxycarbonyl aniline 
• 164596-20-7 4-tert-butoxycarbonylamino-benzoic acid methyl ester 
• 144072-29-7 tert-butyl N-[4-(hydroxymethyl)phenyl]carbamate 
• 762-75-4 tert-butyl formate 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 110969-44-3 4-tert-butyloxycarbonylaminobenzoic acid ethyl ester 

Downstream Products

• 140925-90-2 C₃₁H₄₃N₇O₄ 
• 205590-47-2 (S)-2-(4-tert-Butoxycarbonylamino-benzoylamino)-4-methyl-pentanoic acid methyl ester 
• 180863-61-0 N-(4-N-Boc-aminobenzoyl)-methionine methyl ester 
• 292068-87-2 4-{[4-(4-tert-butoxycarbonylamino-benzoylamino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 292069-58-0 4-{[5-(4-tert-butoxycarbonylamino-benzoylamino)-benzo[b]thiophene-2-carbonyl]-amino}-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 197894-75-0 [4-((R)-9-amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indol-3-ylcarbamoyl)phenyl]carbamic acid tert-butyl ester 
• 292069-28-4 6-[4-(4-tert-butoxycarbonylamino-benzoylamino)-thiophene-2-carbonyl]-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carboxylic acid methyl ester 
• 292069-48-8 4-{[6-(4-tert-butoxycarbonylamino-benzoyl)-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carbonyl]-amino}-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester 
• 191934-25-5 benzyl 4-((tert-butoxycarbonyl)amino)benzoate 
• 327037-49-0 4-[(tert-butoxycarbonyl)amino]-N-(β-phenethyl)benzamide 
• 327037-11-6 4-[(tert-butoxycarbonyl)amino]-N-(benzyl)benzamide 
• 478798-20-8 [4-(piperazine-1-carbonyl)-phenyl]-carbamic acid tert-butyl ester 
• 501088-70-6 8-hydroxyoctyl 4-tert-butoxycarbonylamidobenzoate 

Relevant academic research and scientific papers

Design, synthesis and evaluation of novel indole-2-carboxamides for growth inhibition of Mycobacterium tuberculosis and paediatric brain tumour cells

The omnipresent threat of tuberculosis (TB) and the scant treatment options thereof necessitate the development of new antitubercular agents, preferably working via a novel mechanism of action distinct from the current drugs. Various studies identified th

Liquid-phase synthesis of 2,3-dihydro-4-pyridones: One-pot three-component aza Diels-Alder reaction of Danishefsky's diene with aldehydes and PEG-supported amine

An efficient liquid-phase synthesis technique for the construction of 2,3-dihydro-4-pyridones on soluble polymer support has been developed, which utilized one-pot reaction of Danishefsky's diene with aldehydes and polymer-supported amine.

Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines

Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.

Exploring the ability of dihydropyrimidine-5-carboxamide and 5-benzyl-2,4-diaminopyrimidine-based analogues for the selective inhibition of L. major dihydrofolate reductase

To tackle leishmaniasis, search for efficient therapeutic drug targets should be pursued. Dihydrofolate reductase (DHFR) is considered as a key target for the treatment of leishmaniasis. In current study, we are interested in the design and synthesis of selective antifolates targeting DHFR from L. major. We focused on the development of new antifolates based on 3,4-dihydropyrimidine-2-one and 5-(3,5-dimethoxybenzyl)pyrimidine-2,4-diamine motif. Structure activity relationship (SAR) studies were performed on 4-phenyl ring of dihydropyrimidine (26–30) template. While for 5-(3,5-dimethoxybenzyl)pyrimidine-2,4-diamine, the impact of different amino acids (valine, tryptophan, phenylalanine, and glutamic acid) and two carbon linkers were explored (52–59). The synthesized compounds were assayed against LmDHFR. Compound 59 with the IC50 value of 0.10 μM appeared as potent inhibitors of L. major. Selectivity for parasite DHFR over human DHFR was also determined. Derivatives 55–59 demonstrated excellent selectivity for LmDHFR. Highest selectivity for LmDHFR was shown by compounds 56 (SI = 84.5) and 58 (SI = 87.5). Compounds Antileishmanial activity against L. major and L. donovani promastigotes was also performed. To explore the interaction pattern of the synthesized compounds with biological macromolecules, the docking studies were carried out against homology modelled LmDHFR and hDHFR targets.

Antiglioma Activity of Aryl and Amido-Aryl Acetamidine Derivatives Targeting iNOS: Synthesis and Biological Evaluation

Nitric oxide is an important inflammation mediator with a recognized role in the development of different cancers. Gliomas are primary tumors of the central nervous system with poor prognosis, and the expression of the inducible nitric oxide synthase correlates with the degree of malignancy, changes in vascular reactivity, and neo-angiogenesis. Therefore, targeting the nitric oxide biosynthesis appears as a potential strategy to impair glioma progression. In the present work a set of aryl and amido-aryl acetamidine derivatives were synthesized to obtain new potent and selective inducible nitric oxide synthase inhibitors with improved physicochemical parameters with respect to the previously published molecules. Compound 17 emerged as the most promising inhibitor and was evaluated on C6 rat glioma cell line, showing antiproliferative effects and high selectivity over astrocytes.

Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst

An efficient approach for the Chemoselective N-tert-butoxycarbonylation of a variety of amines using diphenylglycoluril as organocatalyst has been described. For the first time, a plausible mechanism for the N-tert-butoxycarbonylation has been proposed using density functional theory (DFT) calculations supported by NMR studies. The reusability of the organocatalyst and observation of the desired N-Boc protected amines being formed without the formation of side products like urea, oxazolidinone, isocyanate, and N, N-di-Boc derivatives makes the present protocol desirable.

Benzothiazole compounds and medical application

The invention discloses a benzothiazole compound and medical application thereof, particularly relates to a benzothiazole compound shown as a formula I and medical application thereof, and especiallyrelates to application of the benzothiazole compound serving as a USP7C-terminal structural domain regulating agent in medicines for preventing and treating myelodysplastic syndromes and malignant tumors. The benzothiazole compound shown in the formula I or the pharmaceutically acceptable salt or solvate of the benzothiazole compound has strong binding force with USP7C-terminal protein; and the protein level of DNMT1 in tumor cells can be reduced, so that the compound can be applied to the preparation of USP7 regulators, has a remarkable anti-tumor cell proliferation effect, and can be used for preparing medicines for preventing or treating myelodysplastic syndrome and malignant tumors.

INHIBITORS OF CYCLIN-DEPENDENT KINASES

Provided herein are inhibitors of cyclin-dependent kinases (CDKs), pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of diseases.

Polyvalent Diazonium Polymers Provide Efficient Protection of Oncolytic Adenovirus Enadenotucirev from Neutralizing Antibodies while Maintaining Biological Activity in Vitro and in Vivo

Oncolytic viruses offer many advantages for cancer therapy when administered directly to confined solid tumors. However, the systemic delivery of these viruses is problematic because of the host immune response, undesired interactions with blood components, and inherent targeting to the liver. Efficacy of systemically administered viruses has been improved by masking viral surface proteins with polymeric materials resulting in modulation of viral pharmacokinetic profile and accumulation in tumors in vivo. Here we describe a new class of polyvalent reactive polymer based on poly(N-(2-hydroxypropyl)methacrylamide) (polyHPMA) with diazonium reactive groups and their application in the modification of the chimeric group B oncolytic virus enadenotucirev (EnAd). A series of six copolymers with different chain lengths and density of reactive groups was synthesized and used to coat EnAd. Polymer coating was found to be extremely efficient with concentrations as low as 1 mg/mL resulting in complete (>99%) ablation of neutralizing antibody binding. Coating efficiency was found to be dependent on both chain length and reactive group density. Coated viruses were found to have reduced transfection activity both in vitro and in vivo, with greater protection against neutralizing antibodies resulting in lower transgene production. However, in the presence of neutralizing antibodies, some in vivo transgene expression was maintained for coated virus compared to the uncoated control. The decrease in transgene expression was found not to be solely due to lower cellular uptake but due to reduced unpackaging of the virus within the cells and reduced replication, indicating that the polymer coating does not cause permanent inactivation of the virus. These data suggest that virus activity may be modulated by the appropriate design of coating polymers while retaining protection against neutralizing antibodies.

Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone

Selective cytochrome P450 (CYP) 1B1 inhibition has potential as an anticancer strategy that is unrepresented in the current clinical arena. For development of a selective inhibitor, we focused on the complexity caused by sp3-hybridized carbons and synthesized a series of benzo[h]chromone derivatives linked to a non-aromatic B-ring using α-naphthoflavone (ANF) as the lead compound. Ring structure comparison suggested compound 37 as a suitable cyclohexyl-core with improved solubility. Structural evolution of 37 produced the azide-containing cis-49a, which had good properties in three important respects: (1) selectivity for CYP1B1 over CYP1A1 and CYP1A2 (120-times and 150-times, respectively), (2) greater inhibitory potency of >2 times that of ANF, and (3) improved solubility. The corresponding aromatic B-ring compound 59a showed low selectivity and poor solubility. To elucidate the binding mode, we performed X-ray crystal structure analysis, which revealed the interaction mode and explained the subtype selectivity of cis-49a.