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Chemical Structure| 1450754-38-7 Chemical Structure| 1450754-38-7
Chemical Structure| 1450754-38-7

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3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine is a photo-crosslinking probe used to study protein-protein or protein-small molecule interactions.

4.5 *For Research Use Only !

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Product Citations

Product Citations

Webber, Lucas C. ; Anderson, Lindsey N. ; Paraiso, Ines L. ; Metz, Thomas O. ; Bradley, Ryan ; Stevens, Jan F. , et al.

Abstract: Xanthohumol, the principle prenylflavonoid found in hops (Humulus lupulus) and a reported anti-inflammatory agent, has great potential for pharmaceutical interventions related to inflammatory disorders in the gut. A suite of probes was prepared from xanthohumol and its structural isomer isoxanthohumol to enable profiling of both protein affinity binding and catalytic enzyme reactivity. The regiochem. of the reactive group on the probes was altered to reveal how probe structure dictates protein labeling, and which probes best emulate the natural flavonoids. Affinity- and activity-based probes were applied to Escherichia coli, and protein labeling was measured by chemoproteomics. Structurally dependent activity-based probe protein labeling demonstrates how subtle alterations in flavonoid structure and probe reactive groups can result in considerably different protein interactions. This work lays the groundwork to expand upon unexplored cellular activities related to xanthohumol interactions, metabolism, and anti-inflammatory mechanisms.

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Product Details of 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine

CAS No. :1450754-38-7
Formula : C7H9IN2
M.W : 248.06
SMILES Code : ICCC1(CCC#C)N=N1
MDL No. :MFCD29918289
InChI Key :XKVWLCIADFSFAP-UHFFFAOYSA-N
Pubchem ID :118987359

Safety of 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H314
Precautionary Statements:P210-P240-P242-P243-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378-P403+P233-P501
Class:3(8)
UN#:2924
Packing Group:

Application In Synthesis of 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1450754-38-7 ]

[ 1450754-38-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1450754-38-7 ]
  • [ 96145-98-1 ]
  • 5-(2-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)ethoxy)-1-phenyl-3-(trifluoromethyl)-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate; In N,N-dimethyl-formamide; at 24 - 50℃; for 12.5h; A mixture of compound S9 (38.1 mg, 167 tmo1, I equiv) and iodo-diazirine 57 (41.4 mg, 178 p.moi, 1.00 equiv) was dissolved in DMF (1.7 rnL) at 24 C. Potassium carbonate (46.1 rng, 334 imol, 2.00 equiv) was added to the resulting mixture. The reaction mixture was stirred for 12 hours at 50 C, then cooled for 30 minutes to 24 C and partitioned between ethyl acetate (5 mL) and Di water (5 mL). The organic portion was separated and washed with brine (3 x 5 mL). The organic portion was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford an off white powder. The powder was purified by flash column chromatography (20% ethyl acetate-hexanes) to afford the celecoxib analog 9 as a pale yellow oil (39.4 mg, 68%).R= 0.58 (20% ethyl acetate-hexanes; UV). ?HNIvR (500 MHz, CDCI3): d 7.74 (d, 2H, J 7,6 Hz, El3). 7.48 (dd, 2H, J == 7.6, 7.6 Hz, H4), 7.36 (t, IH, J == 7.6, 7.6 Hz, H5), 5.92 (s, IH, Hi), 3.99 (t, 2H, J = 6.0 Hz, H2), 2.01-195 (m, 5H, Ho/HfHc), 1.66 (t, 2H, J = 6.8 Hz, FL). ?3C NMR (125 MHz, CDC13): oe 154.0 (C), 141.8 (q, 2JCF 38.4 Hz, CT:1), 137.5 (C), 129.0 (CH), 127.7 (CH). 123.0 (CH), 120.9 (q, IJCF = 267.3 Hz CF3), 84.7 (q, 3JCF = 2. 1 Hz, CH), 82.4 (C), 69.4 (CH), 67.1 (OCH2), 32.6 (CFL), 32.3 (Cl-i2), 26.1 (CN2), 13.2 (CH3). ?9F NMR (375 MHz, CDCI3): oe -63.3 ppm. [R (ATR-FTIR). cnf?: 3303 (s), 1594 (m). 1562(m), 1508 (rn), 1488 (m), 1457 (m), 1243 (s), 1126 (s), 1099 (s), 968 (s), 759 (s), 639 (s) cm- 1. HRMS-ESI (m/z): [MH-+1j calculated ?for Cv7HT6F3N4O. 34g. 1271; found, 349.1276.
 

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