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[ CAS No. 458-37-7 ] {[proInfo.proName]}

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Chemical Structure| 458-37-7
Chemical Structure| 458-37-7
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Product Citations

Product Citations      Expand+

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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Abstract: Curcumin, a polyphenol extracted from turmeric, has many therapeutic properties. Those benefits make this compound a promissing alternative in medicine that can be used in the treatment of diseases such as arthritis, metabolic syndrome, liver disease, obesity, neurodegenerative illness and multiple types of cancer. Colon cancer is high occurrence disease and it’s the second most letal type of cancer. As chemotherapy has too many side effects, new natural products are widely researched as alternative drugs to treat all kinds of cancer. Curcumin is being researched as a replacement for the traditional chemotherapy drugs, however, it’s instability when ingested makes it unable to reach the colon with treatment potential. Incorporating the compound in a biopolymer is a common strategy to by-pass this problem and allow the drug to reach the desired location. Chitosan is an example of biopolymer which suits this characteristics and can be used to transport the curcumin through the digestive tract. Supercritical impregnation was the technique chosen to incorporate the curcumin into the chitosan, which is a method that utilizes a supercritical fluid technology to achieve this objective. The goal of this work was to impregnate the chitosan particles with curcumin using carbon dioxide expanded in ethanol and evaluate its delivery capacity as well as making the mathematical modeling of the process. SEM and FTIR were used to characterize the particles before and after the impregnation. The pressure of 200 bar resulted in highest percent and amount of curcumin impregnated (15,8% and 3,16 mg) in the particles and there was no significant difference between the quantities of ethanol evaluated. The first order model was the one that best described the curcumin liberation in PBS (pH 7,4).

Keywords: colon cancer ; drug delivery ; CO2 ; mathematical modeling

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Product Details of [ 458-37-7 ]

CAS No. :458-37-7 MDL No. :MFCD00008365
Formula : C21H20O6 Boiling Point : -
Linear Structure Formula :(HOC6H3(OCH3)CHCHCO)2CH2 InChI Key :VFLDPWHFBUODDF-FCXRPNKRSA-N
M.W : 368.38 Pubchem ID :969516
Synonyms :
Diferuloylmethane; Indian Saffron; Turmeric Yellow
Chemical Name :(1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

Calculated chemistry of [ 458-37-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 102.8
TPSA : 93.06 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.27
Log Po/w (XLOGP3) : 3.2
Log Po/w (WLOGP) : 3.15
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : 4.04
Consensus Log Po/w : 3.03

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.94
Solubility : 0.0422 mg/ml ; 0.000115 mol/l
Class : Soluble
Log S (Ali) : -4.83
Solubility : 0.0055 mg/ml ; 0.0000149 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.45
Solubility : 0.0131 mg/ml ; 0.0000356 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.97

Safety of [ 458-37-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 458-37-7 ]

* 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 [ 458-37-7 ]

[ 458-37-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 458-37-7 ]
  • [ 36062-04-1 ]
YieldReaction ConditionsOperation in experiment
92.9% With platinum-iron-nickel hydroxide composite nanoparticle catalyst; In ethanol; at 24℃; for 1h; The platinum - iron-nickel hydroxide composite nano-particle catalyst 1g added curcumin 100 grams,Ethanol 300ml reaction flask, the reaction was stirred at room temperature at 24 ° C for 1 hour, the solvent was evaporated under reduced pressure,98 g pale yellow viscous material was obtained, dissolved in 400 ml ethanol and concentrated to 150 ml,Crystallization was allowed to stand in a freezer to give 92.9 g of a light yellow solid in a yield of 92.9percent.
With hydrogen;palladium; In ethyl acetate; The first series of compounds contained two aryl rings separated by an unsaturated seven carbon spacer having two carbonyls. The aryl rings contained different substituents in various positions on the ring, wherein the structure of the substituents was designed to test the importance of the type of functional group and location on the aryl ring necessary for inhibition. The synthesis of compounds 2a-2i was performed using an aldol type reaction as first described by Pabon (Pabon, H. J. J. 1964. A Synthesis of Curcumin and Related Compounds. Recueil 379-386). 2,4-Pentanedione was reacted with a substituted benzaldehyde (FIG. 2) to give curcumin (2a) or one of its analogs (2b-2i). Two curcumin analogs, 3a and 3b were synthesized from analogs 2a and 2b according to the scheme found in FIG. 2, using palladium on activated charcoal under a hydrogen atmosphere. These compounds contain two aryl rings separated by a saturated seven carbon spacer having two carbonyls and were designed to test the importance of having saturation in the seven carbon spacer. Four additional curcumin analogs, 4b, 5b, 6b, and 7b were synthesized from analog 2b according to the scheme found in FIG. 2. These contain two aryl rings separated by an unsaturated seven carbon spacer having at least one substituent between the carbonyls. These two curcumin analogs were designed to test the importance of substituents on the spacer and on the central methylene carbon. The synthesis of compounds 4b and 5b was performed by addition of a base and an alkyl halide in an SN2 type reaction. The disubstituted compound 5b was formed rather than the monosubstituted compound 7b. Compounds 6b and 7b were prepared, respectively, by reacting 3-methyl-2,4-pentanedione and 3-benzyl-2,4-pentanedione with benzaldehydes in an aldol type reaction.
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; Gingerenone A utilized in the present invention was synthesized by hydrogenating and dehydrating curcumin, which is a natural material extracted from turmeric root according to the process shown in FIG. 1. A constitutional formula of the synthesized compound is identical to the above Formula 1.
  • 2
  • [ 458-37-7 ]
  • [ 36062-05-2 ]
  • [ 36062-04-1 ]
  • [ 36062-07-4 ]
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