4-Nitrobenzyl carbamate | CAS:32339-07-4

4-Nitrobenzyl carbamate

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Description:

4-Nitrobenzyl carbamate-protected aziridines undergo regioselective ring opening to produce β-substituted tryptamines for a series of indoles.

In vitro:

J Med Chem. 2003 Jun 5;46(12):2456-66.

Structure-activity relationships for 4-nitrobenzyl carbamates of 5-aminobenz[e]indoline minor groove alkylating agents as prodrugs for GDEPT in conjunction with E. coli nitroreductase.[Pubmed: 12773049]

METHODS AND RESULTS:
Twelve substituted 4-Nitrobenzyl carbamate prodrugs of the 5-aminobenz[e]indoline class of DNA minor groove alkylating agents were prepared and tested as prodrugs for gene-directed enzyme prodrug therapy (GDEPT) using a two-electron nitroreductase (NTR) from E. coli B. The prodrugs and effectors were tested in a cell line panel comprising parental and transfected human (SKOV/Skov-NTR(neo), WiDr/WiDr-NTR(neo)), Chinese hamster (V79(puro)/V79-NTR(puro)), and murine (EMT6/EMT6-NTR(puro)) cell line pairs. In the human cell line pairs, several analogues bearing neutral methoxyethoxy-, 2-hydroxyethoxy-, or 3-hydroxypropoxy-substituted side chains were good substrates for NTR as measured by cytotoxicity ratios, with NTR-ve/NTR+ve ratios similar to the established NTR substrates CB1954 (an aziridinyl dinitrobenzamide) and the analogous bromomustard. Selectivity for NTR decreased with increasing side-chain size or the presence of a basic amine group. Low to modest selectivity was observed in the Chinese hamster-derived cell line pair; however, in the murine EMT6/EMT6-NTR(puro) cell line pair, the above hydroxyalkoxy analogues again showed significant selectivity for NTR. The activity of the 2-hydroxyethoxy analogue was evaluated against NTR-expressing EMT6 tumors comprising ca. 10% NTR+ve cells at the time of tumor treatment. A small decrease in NTR+ve cells was observed after treatment, with a lesser effect against NTR-ve target cells, but these effects were not statistically significant and were much less than for the dinitrobenzamides.
CONCLUSIONS:
These results suggest that useful GDEPT prodrugs based on the 4-Nitrobenzyl carbamate and 5-aminobenz[e]indoline motifs may be developed if optimization of pharmacokinetics can be addressed.

4-Nitrobenzyl carbamate Description

Source:	The roots of Solanum integrifolium
Solvent:	DMSO, Pyridine, Methanol, Ethanol, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Product Name	4-Nitrobenzyl carbamate
Price:
CAS No.:	32339-07-4
Catalog No.:	CFN92319
Molecular Formula:	C₈H₈N₂O₄
Molecular Weight:	196.2 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	The roots of Solanum integrifolium
Solvent:	DMSO, Pyridine, Methanol, Ethanol, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Alkaloids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.0968 mL	25.4842 mL	50.9684 mL	101.9368 mL	127.421 mL
5 mM	1.0194 mL	5.0968 mL	10.1937 mL	20.3874 mL	25.4842 mL
10 mM	0.5097 mL	2.5484 mL	5.0968 mL	10.1937 mL	12.7421 mL
50 mM	0.1019 mL	0.5097 mL	1.0194 mL	2.0387 mL	2.5484 mL
100 mM	0.051 mL	0.2548 mL	0.5097 mL	1.0194 mL	1.2742 mL

CFN90062	Sorbic acid, 1-p-tolylhydrazide	802048-02-8	216.28	C₁₃H₁₆N₂O
CFN90110	3'-Nitroacetophenone	121-89-1	165.15	C₈H₇NO₃
CFN90093	Propargyl benzenesulfonate	6165-75-9	196.22	C₉H₈O₃S
CFN90120	Propargyl p-toluenesulfonate	6165-76-0	210.25	C₁₀H₁₀O₃S
CFN92317	Carbamic acid	84640-31-3	224.2	C₁₀H₁₂N₂O₄
CFN92318	Ethyl p-nitrobenzyl carbonate	943409-69-6	224.2	C₁₀H₁₂N₂O₄
CFN92319	4-Nitrobenzyl carbamate	32339-07-4	196.2	C₈H₈N₂O₄