21715-90-2 Usage
Description
N-Hydroxy-5-norbornene-2,3-dicarboximide (NHD) is a white to off-white crystalline powder with antiviral activity, particularly against HIV infections. It works by inhibiting the reverse transcriptase enzyme in the virus, blocking the synthesis of viral DNA. NHD also exhibits ferroelectric properties, which can be useful for diagnostic purposes. In animal studies, it has shown effectiveness against cancer cells without toxicity in humans at certain doses.
Uses
Used in Antiviral Applications:
N-Hydroxy-5-norbornene-2,3-dicarboximide is used as an antiviral agent for treating HIV infections. It inhibits the reverse transcriptase enzyme in the virus, blocking the synthesis of viral DNA.
Used in Diagnostic Applications:
The ferroelectric properties of N-Hydroxy-5-norbornene-2,3-dicarboximide make it useful for diagnostic purposes, as changes in its melting point can be observed when mixed with water.
Used in Cancer Treatment:
In animal studies, a dose of 5 mg/kg of N-Hydroxy-5-norbornene-2,3-dicarboximide was found to be effective against cancer cells, with no toxicity observed in humans at doses up to 500 mg/day.
Used in Solution-phase Peptide Synthesis:
N-Hydroxy-5-norbornene-2,3-dicarboximide is used in solution-phase peptide synthesis, particularly in the synthesis of enkephalin analogs.
Used in Inhibiting Racemization:
N-Hydroxy-5-norbornene-2,3-dicarboximide is used to inhibit racemization in peptide synthesis when using DCC as a condensing agent. It also decreases racemization and inhibits the formation of N-acylureas during peptide synthesis.
Optimal Reaction Conditions:
The optimal reaction conditions for N-Hydroxy-5-norbornene-2,3-dicarboximide are a pH of 6 and a temperature of 45 degrees Celsius.
Purification Methods
Dissolve the imide in CHCl3, filter, evaporate and recrystallise from EtOAc. IR (nujol): max 1695, 1710 and 1770 (C=O), and 3100 (OH) cm-1. The O-acetyl derivative has m 113-114o (from EtOH) with IR bands at max 1730, 1770 and 1815 cm-1 only, and the O-benzoyl derivative has m 143-144o (from propan-2-ol or *C6H6). [Bauer & Miarka J Org Chem 24 1293 1959, Fujino et al. Chem Pharm Bull Jpn 22 1857 1974]. [Beilstein 21/10 V 188.]
Check Digit Verification of cas no
The CAS Registry Mumber 21715-90-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,7,1 and 5 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 21715-90:
(7*2)+(6*1)+(5*7)+(4*1)+(3*5)+(2*9)+(1*0)=92
92 % 10 = 2
So 21715-90-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO3/c11-8-6-4-1-2-5(3-4)7(6)9(12)10(8)13/h1-2,4-7,13H,3H2/t4-,5-,6-,7-/m1/s1
21715-90-2Relevant articles and documents
Clarification of stereochemistry aspects for N-hydroxy-5-norbornene-2,3-dicarboximide derivatives and elucidation of them by experimental and theoretical investigations, including the synthesis of N, N'-bis-(5-exo-norbornene-2,3-dicarboxyimidyl) carbonate
Maftei, Elena,Maftei, Catalin V.,Freytag, Matthias,Franz, M. Heiko,Bannenberg, Thomas,Neda, Ion
, p. 245 - 255 (2018/08/04)
Ambiguities about the stereochemistry of N-hydroxy- 5-norbornene-2, 3-dicarboximide and N, N'-bis-(5- norbornene-2, 3-dicarboxyimidyl) carbonate and confusing naming of N-hydroxy-5-norbornene-2, 3- dicarboximide and its corresponding anhydride by literature and chemical sellers were addressed. This considered the stereochemistry itself as well as the description thereof. The unclear points could be elucidated by scientific deliberations and by practical and theoretical experiments. N, N'-bis-(5-exonorbornene- 2, 3-dicarboxyimidyl) carbonate was synthesised for the first time and for comparison, the exo and endo isomer of N-hydroxy-5-norbornene-2, 3-dicarboximide and N, N'-bis-(5-endo-norbornene-2, 3-dicarboxy-imidyl) carbonate were manufactured. The molecular structures of N-hydroxy-5-endo-norbornene-2, 3-dicarboximide and N, N'-bis-(5-endo-norbornene-2, 3-dicarboxyimidyl) carbonate have been investigated by X ray crystallography. The stereochemistry assignments of corresponding exo-endo isomers pairs were studied by various NMR experiments and the thermodynamical heat of formation were calculated by theoretical methods. The exo-endo isomers pairs can be differed easily by the chemical shifts of special atoms. For the 13C-NMR experiment is this salient atom the methylene bridge carbon and in the case of 1H-NMR experiment this role fulfilled by the protons which defines the exo-endo isomerism. Using theoretical concepts, we could illustrate that the exo carbonate is thermodynamically more stable than its corresponding endo isomer. For the exo and endo isomers of N-hydroxy-5-norbornene-2, 3-dicarboximide and their corresponding anhydrides, the exo isomers were just slightly favoured. These results underlined the experimental facts that the equilibration of them ends in a rate of nearly fifty-fifty.
Aminolysis of 2,3-[Cyclopenten-3',5'-diyl]-endo-N-(2",4"-dinitrophenoxy)succinimide with Morpholine, Piperidine, Pyrrolidine and Cyclohexylamine in Ethyl Acetate
Bhattacharhjee, G.,Singh, A. K.,Gupta, Anshu
, p. 49 - 51 (2007/10/03)
-
On the knowledge of N-hydroxy-isoindoles. 33. Report on hydroxylamine-derivatives
Zinner,Düerkop
, p. 776 - 779 (2007/10/08)
-
