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[ CAS No. 121-66-4 ] {[proInfo.proName]}

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Chemical Structure| 121-66-4
Chemical Structure| 121-66-4
Structure of 121-66-4 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations      Expand+

Phelelisiwe S. Dube ; Dylan Hart ; Lesetja J. Legoabe , et al. DOI:

Abstract: Nitrothiazole derivatives have been reported to exhibit activity against aerobic, anaerobic, and microaerophilic bacteria. This activity profile makes the nitrothiazole compound class an ideal lead source against Mycobacterium tuberculosis, which flourishes in varied environments with different oxygen concentrations. In this work, we investigated six nitrothiazole derivatives for antitubercular activity. The compounds exhibited potent activity, with compounds 9 and 10 possessing an equipotent MIC90 value of 0.24 μM. The compounds were investigated for cytotoxicity against HEK293 cells and hemolysis against red blood cells, and they demonstrated no cytotoxicity nor hemolytic effects, suggesting they possess inherent antitubercular activity.

Keywords: nitrothiazole ; Mannich bases ; antitubercular activity ; tuberculosis ; Mycobacterium tuberculosis

Purchased from AmBeed: ; ;

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski , et al. DOI:

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

Purchased from AmBeed: ; ; ; ; ; ; ; ; 62-44-2 ; ; ; ; ; ; ; ; ; ; ; 101-61-1 ; ; ; ; ; 90-94-8 ; ; ; ; ; ; ; ; ; ; ; ; ; 117-39-5 ; ; ; ; ; ; ; ; ;

Dylan Hart ; Lesetja J. Legoabe ; Omobolanle J. Jesumoroti , et al. DOI: PubMed ID:

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

Product Details of [ 121-66-4 ]

CAS No. :121-66-4 MDL No. :MFCD00005326
Formula : C3H3N3O2S Boiling Point : -
Linear Structure Formula :C3HNS(NH2)(NO2) InChI Key :MIHADVKEHAFNPG-UHFFFAOYSA-N
M.W : 145.14 Pubchem ID :8486
Synonyms :

Calculated chemistry of [ 121-66-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.34
TPSA : 112.97 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.64
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : 0.64
Log Po/w (MLOGP) : -1.75
Log Po/w (SILICOS-IT) : -0.38
Consensus Log Po/w : -0.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.61
Solubility : 3.58 mg/ml ; 0.0247 mol/l
Class : Very soluble
Log S (Ali) : -2.78
Solubility : 0.238 mg/ml ; 0.00164 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.29
Solubility : 73.8 mg/ml ; 0.508 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.76

Safety of [ 121-66-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 121-66-4 ]

* 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 [ 121-66-4 ]

[ 121-66-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 121-66-4 ]
  • [ 3034-48-8 ]
YieldReaction ConditionsOperation in experiment
With sodium nitrite; Example 12 3-[(5-nitrothiazol-2-yl)mercapto]-5-phenyl-1,2,4-triazole (SU4390) (Compound 7) The key starting material 2-bromo-5-nitrothiazole was prepared by treating 2-amino-5-nitrothiazole (Aldrich) with sodium nitrite and hydrogen bromide (Fr. Demande 2,015,434, 1970).
With sodium nitrite; Example 1 3-[(5-nitrothiazol-2-yl)mercapto]-5-phenyl-1,2,4-triazole (Compound 1) The starting material 2-bromo-5-nitrothiazole was prepared by treating 2-amino-5-nitrothiazole (Aldrich) with sodium nitrite and hydrogen bromide (Fr. Demande 2,015,434, 1970).
With sodium nitrite; Example 1 3-[(5-nitrothiazol-2-yl)mercapto]-5-phenyl-1,2,4-triazole (Compound 7) The starting material 2-bromo-5-nitrothiazole was prepared by treating 2-amino-5-nitrothiazole (Aldrich) with sodium nitrite and hydrogen bromide (Fr. Demande 2,015,434, 1970).
  • 3
  • [ 121-66-4 ]
  • [ 71-41-0 ]
  • [ 3034-48-8 ]
YieldReaction ConditionsOperation in experiment
60% In water; hydrogen bromide; sodium nitrite; 2-Bromo-5-nitrothiazole To 72.5 g of 2-amino-5-nitrothiazole in 300 mL of 48percent hydrobromic acid and 200 mL of water stirred and cooled to about -10° C. was slowly added, in portions, 51.8 g of sodium nitrite dissolved in 80 mL of water from one addition funnel and 250 mL of n-amyl alcohol from a second addition funnel. The addition of both solutions required about 3 hours. The cooling bath was removed and the mixture allowed to warm to about 15° C. overnight and then stirred at room temperature for 2 hours. The solid was collected by vacuum filtration and steam distilled to give 67 g of crude product. The crude product was recrystallized from hot ethanol to give 61 g (60percent yield) of the 2-bromo-5-nitrothiazole as a yellow solid.
60% In water; hydrogen bromide; sodium nitrite; 2-Bromo-5-nitrothiazole To 72.5 g of 2-amino-5-nitrothiazole in 300 mL of 48percent hydrobromic acid and 200 mL of water stirred and cooled to about -10° C. was slowly added, in portions, 51.8 g of sodium nitrite dissolved in 80 mL of water from one addition funnel and 250 mL of n-amyl alcohol from a second addition funnel. The addition of both solutions required about 3 hours. The cooling bath was removed and the mixture allowed to warm to about 15° C. overnight and then stirred at room temperature for 2 hours. The solid was collected by vacuum filtration and steam distilled to give 67 g of crude product. The crude product was recrystallized from hot ethanol to give 61 g (60percent yield) of the 2-bromo-5-nitrothiazole as a yellow solid.
60% In water; hydrogen bromide; sodium nitrite; 2-Bromo-5-nitrothiazole To 72.5 g of 2-amino-5-nitrothiazole in 300 mL of 48percent hydrobromic acid and 200 mL of water stirred and cooled to about -10° C. was slowly added, in portions, 51.8 g of sodium nitrite dissolved in 80 mL of water from one addition funnel and 250 mL of n-amyl alcohol from a second addition funnel. The addition of both solutions required about 3 hours. The cooling bath was removed and the mixture allowed to warm to about 15° C. overnight and then stirred at room temperature for 2 hours. The solid was collected by vacuum filtration and steam distilled to give 67 g of crude product. The crude product was recrystallized from hot ethanol to give 61 g (60percent yield) of the 2-bromo-5-nitrothiazole as a yellow solid.
  • 4
  • [ 121-66-4 ]
  • [ 448-36-2 ]
  • [ 1276591-27-5 ]
  • 5
  • [ 4100-13-4 ]
  • [ 121-66-4 ]
  • C6H3N5O3S2 [ No CAS ]
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