13795-24-9

Usage

Uses

Benzyl 4-nitrophenyl carbonate may be used in chemical synthesis.

Purification Methods

Dissolve the carbonate in Et2O, wash with H2O (3x) and saturated aqueous NaCl, dry (MgSO4), evaporate this in a vacuum and recrystallise the residue from a small volume of MeOH, m 78-79o. Alternatively dissolve it in Et2O, wash it with N HCl (2x), 0.5N NaHCO3 (4x) then H2O, dry (Na2SO4), evaporate the Et2O and recrystallise the residue from *C6H6/pet ether, m 79-80o. The 2-nitro-isomer has m 27-28o, b 151o/11mm. [Khosla et al. Indian J Chem 5 279 1967, Wolman et al. J Chem Soc (C) 596 1976, Beilstein 6 IV 2277.]

InChI:InChI=1/C14H11NO5/c16-14(19-10-11-4-2-1-3-5-11)20-13-8-6-12(7-9-13)15(17)18/h1-9H,10H2

Upstream product

• 7693-46-1 4-Nitrophenyl chloroformate 
• 100-51-6 benzyl alcohol 
• 100-02-7 4-nitro-phenol 
• 1885-14-9 phenyl chloroformate 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 4467-44-1 N^α-Benzyloxycarbonyl-hydrazinoessigsaeure-ethylester 
• 70889-93-9 N-(2-Benzyloxycarbonylaminoethyl)glycine 
• 1027186-09-9 (6-Benzyloxycarbonylamino-hexylamino)-acetic acid 
• 1168-87-2 benzyloxycarbonylalanine p-nitrophenyl ester 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 3401-37-4 S-benzyl-N-carbobenzoxy-L-cysteine p-nitrophenyl ester 
• 100-02-7 4-nitro-phenol 
• 392328-27-7 (3R,4S)-(+)-N-benzyloxycarbonyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine 
• 392328-26-6 (3S,4R)-(-)-N-benzyloxycarbonyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine 

Relevant academic research and scientific papers

Bifunctional Br?nsted Base Catalyzes Direct Asymmetric Aldol Reaction of α-Keto Amides

The first enantioselective direct cross-aldol reaction of α-keto amides with aldehydes, mediated by a bifunctional ureidopeptide-based Br?nsted base catalyst, is described. The appropriate combination of a tertiary amine base and an aminal, and urea hydro

Synthesis and Biological Evaluation of 10-Substituted Camptothecin Derivatives with Improved Water Solubility and Activity

Despite remarkable clinical achievements, camptothecin (CPT) still suffers from poor solubility and severe toxicity. Therefore, it is necessary to redevelop CPT derivatives as supplementary antitumor agents with good water solubility and small side effects. In this work, 27 camptothecin derivatives were synthesized and screened for their cytotoxicity against A549 (lung) and HCT-116 (colon) cancer cell lines. Among them, compound B7, 7-ethyl-10-(2-oxo-2-(4-methylpiperidin-1-yl)ethoxy)camptothecin,was demonstrated in vitro to be a more potent antitumor agent than SN-38 by comparison of their inhibitory activities against cell proliferation and colony formation and interference effect on process of cell cycle and cell apoptosis. Additionally, a molecular docking model revealed that B7 can interact with the topoisomerase I–DNA complex, and that the solubility of B7 reached 5.73 μg/mL in water. Moreover, B7 significantly inhibited tumor growth in an A549 xenograft model at dosages of 0.4 and 2.0 mg/kg, and exhibited minimum lethal doses comparable to those of irinotecan. These results indicated that B7, with improved solubility, enhanced activity and acceptable acute toxicity, can be used as a lead compound for the development of novel anticancer agents.

Discovery of a dual tubulin polymerization and cell division cycle 20 homologue inhibitor via structural modification on apcin

Apcin is one of the few compounds that have been previously reported as a Cdc20 specific inhibitor, although Cdc20 is a very promising drug target. We reported here the design, synthesis, and biological evaluations of 2,2,2-trichloro-1-aryl carbamate derivatives as Cdc20 inhibitors. Among these derivatives, compound 9f was much more efficient than the positive compound apcin in inhibiting cancer cell growth, but it had approximately the same binding affinity with apcin in SPR assays. It is possible that another mechanism of action might exist. Further evidence demonstrated that compound 9f also inhibited tubulin polymerization, disorganized the microtubule network, and blocked the cell cycle at the M phase with changes in the expression of cyclins. Thus, it induced apoptosis through the activation of caspase-3 and PARP. In addition, compound 9f inhibited cell migration and invasion in a concentration-dependent manner. These results provide guidance for developing the current series as potential new anticancer therapeutics.

Intracellular delivery of therapeutic proteins through N-Terminal site-specific modification

A versatile strategy for the intracellular delivery of functional proteins/antibodies was developed using N-Terminal site-specific modification. Adopting orthogonal dual-labeling strategies, a cell-permeable RNase A prodrug was designed complementing N-Te

External-Radiation-Induced Local Hydroxylation Enables Remote Release of Functional Molecules in Tumors

Radiation-induced cleavage for controlled release in vivo is yet to be established. We demonstrate the use of 3,5-dihydroxybenzyl carbamate (DHBC) as a masking group that is selectively and efficiently removed by external radiation in vitro and in vivo. D

BIOORTHOGONAL COMPOUNDS COMPRISING A PROPARGYL GROUP FOR TREATING CANCER

A method of preparing an active agent or a salt thereof from a prodrug first compound (1) comprising a propargyl group connected to an oxygen that is directly or indirectly connected to the active agent is provided, wherein the bond between the propargyl group and the oxygen is cleaved by reacting the first compound with palladium or gold, thereby releasing the active agent. Prodrug compositions suitable for use in the method are also provided.

Development of potent and selective tissue transglutaminase inhibitors: Their effect on TG2 function and application in pathological conditions

Potent-selective peptidomimetic inhibitors of tissue transglutaminase (TG2) were developed through a combination of protein-ligand docking and molecular dynamic techniques. Derivatives of these inhibitors were made with the aim of specific TG2 targeting to the intra- and extracellular space. A cell-permeable fluorescently labeled derivative enabled detection of in situ cellular TG2 activity in human umbilical cord endothelial cells and TG2-transduced NIH3T3 cells, which could be enhanced by treatment of cells with ionomycin. Reaction of TG2 with this fluorescent inhibitor in NIH3T3 cells resulted in loss of binding of TG2 to cell surface syndecan-4 and inhibition of translocation of the enzyme into the extracellular matrix, with a parallel reduction in fibronectin deposition. In human umbilical cord endothelial cells, this same fluorescent inhibitor also demonstrated a reduction in fibronectin deposition, cell motility, and cord formation in Matrigel. Use of the same inhibitor in a mouse model of hypertensive nephrosclerosis showed over a 40% reduction in collagen deposition.

NEW COMPOUNDS I

The present invention relates to compounds of formula (I) and their pharmaceutically acceptable salts, solvates, hydrates, geometrical isomers, tautomers, optical isomers or N-oxides, which are inhibitors of SSAO activity. The invention further relates to

PEPTIDIC THROMBIN INHIBITOR COMPOUND

The present invention relates to a novel thrombin inhibitor compound which has a good inhibitory effect against thrombosis and can be orally administered, a process for preparing the same, and to a composition for the therapeutic and/or prophylactic treatment of various diseases associated with thrombin inhibition mechanism, which comprises the same as an active ingredient.

The synthesis and biological evaluation of a series of potent dual inhibitors of farnesyl and geranyl-Geranyl protein transferases.

We have prepared a series of potent, dual inhibitors of the prenyl transferases farnesyl protein transferase (FPTase) and geranyl-geranyl protein transferase I (GGPTase). The compounds were shown to possess potent activity against both enzymes in cell cul