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Chemical Structure| 30626-03-0 Chemical Structure| 30626-03-0

Structure of 30626-03-0

Chemical Structure| 30626-03-0

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Product Citations

Product Citations

du Preez, Charne ; Legoabe, Lesetja J. ; Jordaan, Audrey ; Jesumoroti, Omobolanle J. ; Warner, Digby F. ; Beteck, Richard M.

Abstract: Curcumin is a natural product that has been reported to exhibit myriad pharmacol. properties, one of which is antitubercular activity. It demonstrates antitubercular activity by directly inhibiting Mycobacterium tuberculosis (M.tb) and also enhances immune responses that ultimately lead to the elimination of M.tb by macrophages. This natural product is, however, unstable, and several analogs, noticeably monocarbonyl analogs, have been synthesized to overcome this challenge. Curcumin and its monocarbonyl analogs reported so far exhibit moderate antitubercular activity in the range of 7 to 16 μM. Herein, we report a straightforward synthesis of novel monocarbonyl curcumin analogs, their antitubercular activity, and the structure-activity relationship. The hit compound from this study, 3a, exhibits potent MIC90 values in the range of 0.2 to 0.9 μM in both ADC and CAS media.

Keywords: analogues ; aryl nitro ; curcumin ; synthesis ; tuberculosis

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Product Details of [ 30626-03-0 ]

CAS No. :30626-03-0
Formula : C10H9ClO
M.W : 180.63
SMILES Code : CC(/C=C/C1=CC=C(Cl)C=C1)=O
MDL No. :N/A

Safety of [ 30626-03-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 30626-03-0 ]

* 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 [ 30626-03-0 ]

[ 30626-03-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 50-00-0 ]
  • [ 30626-03-0 ]
  • [ 80567-00-6 ]
  • 5-(2,6-dimethylmorpholinyl)-1-(4-chlorophenyl)-1-penten-3-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.8% 0.303g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.4g (13mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 2hr. After the solid was dissolved, 0.36g (2.0mmol) of 4-(4-chlorophenyl)-3-buten-2-one (prepared as described in preparation 1) was added to the above reaction mixture. The solution was further refluxed and stirred for 13hr. TLC showed the reaction was completed. After cooling with ice-water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol and dried to give 0.37g of white crystals, yield: 53.8 % , mp: 218-220C. 1HNMRδppm (DMSO-d6): 1.09(d, 6H, J=6.6Hz, 2 x CHCH3), 2.47-2.68 (m, 6H, 3NCH2), 3.24-3.46(t, 2H, COCH2), 3.95(q, 2H, J=6.6Hz, 2 x CHCH3), 6.92(d, 1H, J=16.2Hz, =CHCO), 7.49(d, 2H, J=8.4Hz, ArHAA'), 7.69(d, 1H, J=16.2Hz, CH=), 7.79(d, 2H, J=8.4Hz, ArHBB'). MS (m/z): 307(M+, 20), 192(M+-114-H, 24), 165(M+-142, 60).
  • 2
  • [ 25475-67-6 ]
  • [ 30626-03-0 ]
  • [ 1505454-53-4 ]
  • 3
  • [ 4139-61-1 ]
  • [ 30626-03-0 ]
  • (R)-6-bromo-3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxychromen-2-one [ No CAS ]
  • 6-bromo-3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxychromen-2-one [ No CAS ]
 

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