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Chemical Structure| 552-89-6 Chemical Structure| 552-89-6
Chemical Structure| 552-89-6

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CAS No.: 552-89-6

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Jooste, Joelien ; Legoabe, Lesetja J ; Ilbeigi, Kayhan , et al.

Abstract: Geraniol, a primary component of several essential oils, has been associated with broad-spectrum antiprotozoal activities, although moderate to weak. This study primarily concentrated on the synthesis of hydrazinated geraniol derivatives aspotential antiprotozoal agents. The synthesised compounds were tested in vitro against different parasitic protozoans of clinical relevance, including Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense, Trypanosoma cruzi and Leishmania infantum. Compounds 6, 8, 13, 14 and 15 demonstrated low micromolar activity against the different parasites. Compounds 8, 13, 14 and 15 had the highest efficacy against Trypanosoma brucei rhodesiense, as indicated by their respective IC50 values of 0.74, 0.56, 1.26 and 1.00 μM. Compounds 6, 14 and 15 displayed the best activity against Trypanosoma brucei brucei, with IC50 values of 1.49, 1.48 and 1.85 μM, respectively. The activity of compounds 6, 14 and 15 also extended to intracellular Trypanosoma cruzi, with IC50 values of 5.14, 6.30 and 4.90 μM, respectively. Compound 6, with an IC50 value of 11.73 μM, and compound 14, with an IC50 value of 8.14 μM, demonstrated some modest antileishmanial activity.

Keywords: geraniol ; Leishmania infantum ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense ; Trypanosoma cruzi

Purchased from AmBeed: ; ; ; ;

du Preez, Charne ; Legoabe, Lesetja J. ; Jordaan, Audrey , et al.

DOI: PubMed ID:

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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Dylan Hart ; Lesetja J. Legoabe ; Omobolanle J. Jesumoroti , et al.

Abstract: Herein we report the synthesis of novel compounds inspired by the antimicrobial activities of nitroazole and thiazolidin-4-one based compounds reported in the literature. Target compounds were investigated in?vitro for antitubercular, antibacterial, antifungal, and overt cell toxicity properties. All compounds exhibited potent antitubercular activity. Most compounds exhibited low micromolar activity against S. aureus and C. albicans with no overt cell toxicity against HEK-293 cells nor haemolysis against human red blood cells. Notably, compound 3b exhibited low to sub-micromolar activities against Mtb, MRSA, and C. albicans. 3b showed superior activity (0.25?μg/ml) against MRSA compared to vancomycin (1?μg/ml).

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; 591-31-1 ; ; ; ; ; 123-08-0 ; 100-52-7 ; ; 89-98-5

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Product Details of [ 552-89-6 ]

CAS No. :552-89-6
Formula : C7H5NO3
M.W : 151.12
SMILES Code : O=CC1=CC=CC=C1N(=O)=O
MDL No. :MFCD00007132
InChI Key :CMWKITSNTDAEDT-UHFFFAOYSA-N
Pubchem ID :11101

Safety of [ 552-89-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335-H412
Precautionary Statements:P261-P264-P270-P271-P273-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Application In Synthesis [ 552-89-6 ]

* 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.

  • Upstream synthesis route of [ 552-89-6 ]
  • Downstream synthetic route of [ 552-89-6 ]

[ 552-89-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 552-89-6 ]
  • [ 142273-20-9 ]
References: [1] Synthesis (Germany), 2017, vol. 49, # 18, p. 4247 - 4253.
 

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