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Aziridines information


Mitomycin C, an aziridine, is used as a chemotherapeutic agent by virtue of its antitumour activity.[1]

In organic chemistry, aziridines are organic compounds containing the aziridine functional group (chemical structure (R−)4C2N−R), a three-membered heterocycle with one amine (>NR) and two methylene bridges (>CR2).[2][3][4] The parent compound is aziridine (or ethylene imine), with molecular formula C2H4NH. Several drugs feature aziridine rings, including mitomycin C, porfiromycin, and azinomycin B (carzinophilin).[5]

  1. ^ Tomasz, Maria (September 1995). "Mitomycin C: small, fast and deadly (but very selective)". Chemistry and Biology. 2 (9): 575–579. doi:10.1016/1074-5521(95)90120-5. PMID 9383461.
  2. ^ Gilchrist, T.L. (1987). Heterocyclic chemistry. ISBN 978-0-582-01421-3.
  3. ^ Epoxides and Aziridines – A Mini Review Albert Padwa and S. Shaun Murphree Arkivoc (JC-1522R) pp. 6–33 Online article
  4. ^ Sweeney, J. B. (2002). "Aziridines: Epoxides' ugly cousins?". Chem. Soc. Rev. 31 (5): 247–258. doi:10.1039/B006015L. PMID 12357722.
  5. ^ Ismail, Fyaz M.D.; Levitsky, Dmitri O.; Dembitsky, Valery M. (2009). "Aziridine alkaloids as potential therapeutic agents". European Journal of Medicinal Chemistry. 44 (9): 3373–3387. doi:10.1016/j.ejmech.2009.05.013. PMID 19540628.

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Aziridine

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practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest...

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Aziridines

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In organic chemistry, aziridines are organic compounds containing the aziridine functional group (chemical structure (R−)4C2N−R), a three-membered heterocycle...

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Azomethine ylide

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pharmaceuticals. Azomethine ylides can be generated from many sources, including aziridines, imines, and iminiums. They are often generated in situ, and immediately...

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Nitrene

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isoindole: Nitrene cycloaddition. With alkenes, nitrenes react to form aziridines, very often with nitrenoid precursors such as nosyl- or tosyl-substituted...

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Allylic rearrangement

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unusual conversion of 1-alkyl-2-(bromomethyl)aziridines into 1-alkyl-2-(N-alkyl-N-ethylaminomethyl)aziridines using methyllithium Matthias D'hooghe and Norbert...

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Organic azide

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Chloride Promoted Highly Regioselective Ring Opening of Epoxides and Aziridines Using NaN 3 in Acetonitrile: A Facile Synthesis of 1,2-Azidoalcohols and...

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Coupling reaction

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(2013-08-20). "Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines". Journal of the American Chemical Society. 135 (36): 13605–13609. doi:10...

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Aziridinium

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Aziridiniums are the ionic form of the class of molecules known as aziridines. Aziridines can be used to insert nitrogen atoms during synthesis, but without...

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De Kimpe aziridine synthesis

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3-tetrasubstituted aziridines from α-chloroketimines". Tetrahedron. 46 (8): 2965–2974. doi:10.1016/S0040-4020(01)88388-5. "Asymmetric Synthesis of Aziridines by Reduction...

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Malignancy

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oxazaphosphorines, alkyl alkane, sulphonates, nitrosoureas, tetrazines and aziridines." Malignancy has been a constant global health concern for a number of...

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Ring strain

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cyclobutanes, cyclobutenes, [1,1,1]propellanes, [2,2,2]propellanes, epoxides, aziridines, cyclopentenes, and norbornenes. These molecules have bond angles between...

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Amine

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R″ groups are constrained in cyclic structures such as N-substituted aziridines (quaternary ammonium salts are resolvable). In aromatic amines ("anilines")...

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Imine

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of an epoxide. Thus, ethylenimine is the three-membered ring species aziridine C2H4NH. The relationship of imines to amines having double and single...

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Taurine

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aqueous sodium bisulfite. A direct approach involves the reaction of aziridine with sulfurous acid. In 1993, about 5000–6000 tonnes of taurine were produced...

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Tretinoin

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Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine Platinum-based Carboplatin#...

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Payne rearrangement

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"forward" (epoxide to aziridine) or "reverse" (aziridine to epoxide) direction depending on the conditions employed. Electron-poor aziridines undergo the reverse...

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Sodium amide

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as in the preparation of methylenecyclopropane below. Cyclopropenes, aziridines and cyclobutanes may be formed in a similar manner. Carbon acids which...

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Hydroxycarbamide

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Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine Platinum-based Carboplatin#...

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Methotrexate

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Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine Platinum-based Carboplatin#...

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Amine alkylation

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ammonia. Intramolecular reactions of haloamines X-(CH2)n-NH2 give cyclic aziridines, azetidines and pyrrolidines. N-alkylation is a general and useful route...

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Ylide

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aldehyde or by thermal ring opening reaction of certain N-substituted aziridines. The further-unsaturated nitrile ylides are known almost exclusively as...

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Cancer immunotherapy

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Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine Platinum-based Carboplatin#...

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Gemcitabine

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Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine Platinum-based Carboplatin#...

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Chemotherapy

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alkylating agents are the nitrogen mustards, nitrosoureas, tetrazines, aziridines, cisplatins and derivatives, and non-classical alkylating agents. Nitrogen...

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Oximide

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The chemical formula is C2HNO2. Its core is a three member heterocycle, aziridine. In 1886 Ost and Mente claimed to produce oximide by the reaction of oxamic...

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