20576-82-3

Usage

Uses

Used in Pharmaceutical Industry:
4-(TERT-BUTOXYCARBONYL)BENZOIC ACID is used as a synthetic intermediate for the development of pyrrolidinone analogs. These analogs act as potential 20S proteasome inhibitors, which are crucial in the regulation of cellular processes such as protein degradation and cell cycle progression. Inhibition of the 20S proteasome can lead to the disruption of these processes, making it a promising approach for the treatment of various diseases, including cancer.
In the synthesis of pyrrolidinone analogs, 4-(TERT-BUTOXYCARBONYL)BENZOIC ACID serves as a key building block, providing the necessary structural framework for the development of these potential therapeutic agents. The compound's reactivity and functional groups enable the formation of various derivatives, which can be further optimized for improved potency and selectivity against the 20S proteasome.
Additionally, 4-(TERT-BUTOXYCARBONYL)BENZOIC ACID may also find applications in other industries, such as materials science, where its unique chemical properties could be utilized for the development of novel materials with specific properties. However, further research and development would be required to explore these potential applications fully.

InChI:InChI=1/C12H14O4/c1-12(2,3)16-11(15)9-6-4-8(5-7-9)10(13)14/h4-7H,1-3H3,(H,13,14)

Upstream product

• 28313-42-0 di-tert-butyl terephthalate 
• 100-20-9 terephthaloyl chloride 
• 100-21-0 terephthalic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 619-66-9 4-Carboxybenzaldehyde 
• 75-65-0 tert-butyl alcohol 
• 65874-27-3 4-(tert-butoxycarbonyl)benzaldehyde 

Downstream Products

• 554-68-7 triethylamine hydrochloride 
• 166977-31-7 4-[[(5,6-Dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)oxy]carbonyl]benzoic acid, tert-butyl ester 
• 1307310-03-7 tert-butyl (2-(3-(2-cyclohexylethyl)phenyl)-2-oxoethyl)terephthalate 
• 1307310-06-0 C₂₄H₂₆N₂O₂ 
• 1307310-12-8 C₁₂H₁₅NO₃ 
• 1307310-15-1 C₂₄H₂₅NO₂S 
• 1307310-04-8 tert-butyl 4-(4-(3-(2-cyclohexylethyl)phenyl)-1H-imidazol-2-yl)benzoate 
• 1307310-05-9 (S)-1-(4-(4-(3-(2-cyclohexylethyl)phenyl)-1H-imidazol-2-yl)benzoyl)pyrrolidine-2-carbonitrile 
• 1307310-07-1 (S)-1-(4-(4-(3-(2-cyclohexylethyl)phenyl)-1H-imidazol-2-yl)benzoyl)pyrrolidine-2-carboximidamide hydrochloride 
• 1307310-08-2 4-(4-(3-(2-cyclohexylethyl)phenyl)oxazol-2-yl)benzoic acid 
• 1307310-09-3 (S)-1-(4-(4-(3-(2-cyclohexylethyl)phenyl)oxazol-2-yl)benzoyl)pyrrolidine-2-carbonitrile 
• 1307310-10-6 (S)-1-(4-(4-(3-(2-cyclohexylethyl)phenyl)oxazol-2-yl)benzoyl)pyrrolidine-2-carboximidamide hydrochloride 
• 1307310-11-7 tert-butyl 4-carbamothioylbenzoate 
• 1307310-13-9 tert-butyl 4-(4-(3-(2-cyclohexylethyl)phenyl)thiazol-2-yl)benzoate 

Relevant academic research and scientific papers

Unraveling the Self-Assembly Modes in Multicomponent Supramolecular Gels Using Single-Crystal X-ray Diffraction

The control and prediction of the self-assembly process in multicomponent supramolecular gels are challenging because the structure and properties rely mostly on the geometry and spatial arrangement of the building blocks. The understanding of noncovalent

ANTICANCER AGENT DELIVERY MOLECULE

PROBLEM TO BE SOLVED: To provide a compound which can be used as an anticancer agent targeting a cancer cell that highly expresses Lysine-specific demethylase 1 (LSD1) or salt thereof. SOLUTION: The present invention provides a compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof, where Ar, R1, R2, L, Z, p, q, *1 and *2 are as defined in the specifications. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Synthesis and biological activity of optimized belactosin C congeners

Successful biochemical studies of the natural products belactosin A and C as well as their more stable acylated derivatives have proved them to be powerful proteasome inhibitors and thereby potential candidates as pharmacologically relevant active compoun

Development of amidine-based sphingosine kinase 1 nanomolar inhibitors and reduction of sphingosine 1-phosphate in human leukemia cells

Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.

Creation of superior carboxyfluorescein dyes by blocking donor-excited photoinduced electron transfer

(Chemical Equation Presented) Carboxyfluoresceins are widely utilized as fluorescence labeling reagents, but we recently found that their emission intensity is markedly decreased after esterification. On the basis of our hypothesis that the fluorescence d

Process for preparation of dicarboxylic acid monoesters

A process for producing a dicarboxylic acid monoester which comprises subjecting a dicarboxylic acid monoester or an alkali metal salt of a dicarboxylic acid monoester and a metal alkoxide to transesterification in the presence of an organic solvent, or a process for producing a dicarboxylic acid monoester which comprises subjecting a dicarboxylic acid monoester or an alkali metal salt of a dicarboxylic acid monoester and an alcohol to transesterification in the presence of a metal alkoxide.

Design, synthesis, and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen

A homology derived molecular model of prostate specific antigen (PSA) was created and refined. The active site region was investigated for specific interacting functionality and a binding model postulated for the novel 2-azetidinone acyl enzyme inhibitor 1 (IC50 = 8.98 ± 0.90 μM) which was used as a lead compound in this study. A single low energy conformation structure II (Figure 2) was adopted as most likely to represent binding after minimization and dynamics calculations. Systematic analysis of the binding importance of all three side chains appended to the 2-azetidinone was conducted by the synthesis of several analogues. A proposed salt bridge to Lys-145 with 4 (IC50 = 5.84 ± 0.92 μM) gave improved inhibition, but generally the binding of the N-1 side chain in a specific secondary aromatic binding site did not tolerate much structural alteration. A hydrophobic interaction of the C-4 side chain afforded inhibitor 6 (IC50 = 1.43 ± 0.19 μM), and polar functionality could also be added in a proposed interaction with Gln-166 in 5 (IC50 = 1.34 ± 0.05 μM). Reversal of the C-4 ester connectivity furnished inhibitors 7 (IC50 = 1.59 ± 0.15 μM), 11 IC50 = 3.08 ± 0.41 μM) and 13 (IC50 = 2.19 ± 0.36 Mμ) which were perceived to bind to PSA by a rotation of 180° relative to the C-4 ester of normal connectivity. Incorporation of hydroxyl functionality into the C-3 side chain provided 16 IC50 = 348 ± 50 nM) with the greatest increase in PSA inhibition by a single modification. Multiple copy simultaneous search (MCSS) analysis of the PSA active site further supported our model and suggested that 18 would bind strongly. Asymmetric synthesis yielded 18 (IC50 = 226 ± 10 nM) as the most potent inhibitor of PSA reported to date. It is concluded that our design approach has been successful in developing PSA inhibitors and could also be applied to the inhibition of other enzymes, especially in the absence of crystallographic information.

Computational predictions of binding affinities to dihydrofolate reductase: Synthesis and biological evaluation of methotrexate analogues

The relative binding affinities to human dihydrofolate reductase of four new potential antifolates, containing ester linkages between the two aromatic systems, were estimated by free energy perturbation simulations. The ester analogue, predicted to exhibi

Retinoid-like compounds

The present invention relates to a compound of formula I STR1 or a nontoxic pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof, in whichX is --O--CO--, --NH--CO--, --CS--NH--, --CO--O--, --CO--NH--, --COS--, --SCO--, --SCH 2 --, --CH 2 --CH 2 --, --C C--, --CH 2 --NH--, --COCH 2 --, --NHCS--, --CH 2 S--, --CH 2 O--, --OCH 2 --, --NHCH 2 -- or --CR 5 CR 6 --;R m and R k are independently hydrogen, halogen, C 1-6 alkyl, hydroxy, C 1-6 alkyloxy or nitro;n is zero or one;R 4 is --(CH 2) t --Y, C 1-6 alkyl, or C 3-6 cycloalkyl;R 1 is --CO 2 Z, C 1-6 alkyl, CH 2 OH, --CONHR y, or CHO;R 2 and R 3 are independently hydrogen or C 1-6 alkyl;R a and R b are independently hydrogen or C 1-6 alkyl; but when n is one, R a and R b together can form a radical of the formula STR2 Y is naphthyl or phenyl, both radicals can be optionally substituted with one to three same or different C 1-6 alkyl or halogen;Z is hydrogen or C 1-6 alkyl;R 5, R 6 and R y are independently hydrogen or C 1-6 alkyl; andt is zero to six.

Retinoid-like compounds

The present invention relates to a compound of formula STR1 or a nontoxic pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof, in which X is --O--CO--, --NH--CO--, --CS--NH--, --CO--O--, --CO--NH--, --COS--, --SCO--, --SCH2 --, --CH2 --CH2 --, --C C--, --CH2 --NH--, --COCH2 --, --NHCS--, --CH2 S--, --CH2 O--, --OCH2 --, --NHCH2 -- or --CR5 =CR6 --; Rm and Rk are independently hydrogen, halogen, C1-6 alkyl, hydroxy, C1-6 alkyloxy or nitro; n is zero or one; R4 is --(CH2)t --Y, C1-6 alkyl, or C3-6 cycloalkyl; R1 is --CO2 Z, C1-6 alkyl, CH2 OH, --CONHRy, or CHO; R2 and R3 are independently hydrogen or C1-6 alkyl; Ra and Rb are independently hydrogen or C1-6 alkyl; but when n is one, Ra and Rb together can form a radical of the formula STR2 Y is naphthyl or phenyl, both radicals can be optionally substituted with one to three same or different C1-6 alkyl or halogen; Z is hydrogen or C1-6 alkyl; R5, R6 and Ry are independently hydrogen or C1-6 alkyl; and t is zero to six.