Acrylamidine
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| Category | Antibiotics |
| Catalog number | BBF-00019 |
| CAS | 19408-49-2 |
| Molecular Weight | 70.09 |
| Molecular Formula | C3H6N2 |
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Description
Acrylamidine is an antibiotic isolated from Streptomyces sp. D274-2. Acrylamidine has weak antifungal and yeast activity, 50mg/ml inhibits HeLa cells, 100mg/mL inhibits the growth of Yoshida sarcoma, but has no effect on Ehrlich ascites, sarcoma 180, and L-1210.
Specification
| Synonyms | Prop-2-enimidamide; Acrylamidine polymers |
| IUPAC Name | prop-2-enimidamide |
| Canonical SMILES | C=CC(=N)N |
| InChI | InChI=1S/C3H6N2/c1-2-3(4)5/h2H,1H2,(H3,4,5) |
| InChI Key | AXPUQAAUHKSVKR-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | fungi; yeast |
| Melting Point | 138.5-139.5°C |
Reference Reading
1. Pd-catalyzed one-pot synthesis of polysubstituted acrylamidines from isocyanides, diazo compounds, and imines
Xu Yan, Jinxi Liao, Yongzhi Lu, Jinsong Liu, Youlin Zeng, Qian Cai Org Lett. 2013 May 17;15(10):2478-81. doi: 10.1021/ol4009552. Epub 2013 May 3.
A novel and efficient Pd-catalyzed one-pot reaction of ethyl diazoacetate, isocyanides, and imines for the synthesis of acrylamidines was developed. The multicomponent reaction may have occurred through an unpredicted ring-opening process of the ketenimine-imine [2 + 2] intermediate to form the acrylamidine products.
2. Radiosynthesis of (E)-N-(2-[11C]methoxybenzyl)-3-phenyl-acrylamidine, a novel subnanomolar NR2B subtype-selective NMDA receptor antagonist
Cyrille Thominiaux, Béatrice de Bruin, Yann Bramoullé, Françoise Hinnen, Stéphane Demphel, Heric Valette, Michel Bottlaender, Laurent Besret, Michael Kassiou, Frédéric Dollé Appl Radiat Isot. 2006 Mar;64(3):348-54. doi: 10.1016/j.apradiso.2005.08.005. Epub 2005 Nov 22.
Recently, a novel series of amidines has been described, exhibiting high NR2B-subtype selective N-methyl-D-aspartate (NMDA) antagonist activity with nanomolar or subnanomolar affinity. Within the styrylamidine subclass, (E)-N-(2-methoxybenzyl)-3-phenyl-acrylamidine (1), displayed the highest affinity (Ki=0.7 nM versus [(3)H]ifenprodil) and was considered an appropriate candidate for isotopic labelling with carbon-11 (T(1/2): 20.38 min) at its methoxy group for imaging of NMDA receptors with PET. Derivative 1 has been labelled from the corresponding nor-analogue using [(11)C]methyl triflate and the following experimental conditions : (1) trapping at -10 degrees C of [(11)C]methyl triflate in 300 microL of acetone containing 0.6-0.8 mg of precursor 5 (2.4-3.2 micromol) and 5 microL of a 3M solution of NaOH in water (about 5 eq.); (2) concentration to dryness of the reaction mixture (at 110 degrees C, using a helium stream for 1-2 min); (3) taking up the residue with 0.5 mL of the HPLC mobile phase and (4) purification using semi-preparative HPLC (SymmetryPrep) C-18, Waters, 300 x 7.8 mm). Typically, starting from a 1.5 Ci (55.5 GBq) [(11)C]CO(2) production batch, 120-240 m Ci (4.44-8.88 GBq) of [(11)C]-1 (20-40% decay-corrected radiochemical yield, n=5) was obtained within a total synthesis time of 25-30 min. Specific radioactivities ranged from 0.8 to 1.2 Ci/micromol (29.6-44.4 GBq/micromol) at the end of radiosynthesis. No attempts were made to further optimise these reactions, as sufficient material was obtained to allow for preliminary pharmacological characterisation.
3. Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars
Sure Siva Prasad, Soundararasu Senthilkumar, Akriti Srivastava, Sundarababu Baskaran Org Lett. 2017 Aug 18;19(16):4403-4406. doi: 10.1021/acs.orglett.7b02175. Epub 2017 Aug 7.
An efficient one-pot method for the stereoselective synthesis of novel iminosugar C-nitromethyl glycosides is described. This new class of iminosugar glycosides has versatile nitromethyl functionality whose utility was further demonstrated in the single-step synthesis of bicyclic iminosugars. Under reagent-free conditions, the N-allyl-C-nitromethyl glycosides resulted in intramolecular cyclization to iminosugar-oximes, whereas under SET oxidation, they furnished cyclopropane-fused iminosugars. The N-propargyl-C-nitromethyl glycosides underwent an unprecedented ketenimine-acrylamidine-Michael addition cascade reaction to give bicyclic amidines.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
