Home Cart Sign in  
Chemical Structure| 34604-60-9 Chemical Structure| 34604-60-9
Chemical Structure| 34604-60-9

5-Hydroxypyrazine-2-Carboxylic Acid

CAS No.: 34604-60-9

5-Hydroxypyrazine-2-Carboxylic acid, a metabolite of pyrazinamide, is versatile building block for synthesis of antituberculous agents.

4.5 *For Research Use Only !

Cat. No.: A219158 Purity: 98%

Change View

Size Price

US Stock

Global Stock

In Stock
1mg łÇʶÊÊ Inquiry Inquiry
5g łËʶÊÊ Inquiry Inquiry
25g łÿ§¶ÊÊ Inquiry Inquiry
100g łÇď˶ÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1mg

    łÇʶÊÊ

  • 5g

    łËʶÊÊ

  • 25g

    łÿ§¶ÊÊ

  • 100g

    łÇď˶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Product Citations      Show More

Gregory R. Armel ; James T. Brosnan ; Nilda R. Burgos ; Peter J. Porpiglia ; Jose J. Vargas ;

Abstract: Numerous similarities exist between the structure–activity relationships of pharmaceutical drugs and pesticides, creating the potential for finding new crop management tools with novel mechanisms of action. Analogues of pyrazinamide and its active metabolite pyrazinoic acid were evaluated on a variety of monocot and dicot species to assess their potential as commercial herbicides. Six analogues, applied postemergence at 3 kg ai/ha, controlled yellow nutsedge (Cyperus esculentus) ≥ the commercial standards bentazon or imazethapyr. The compound 5-fluoropyrazine-2-carboxylic acid provided between 71 and 95% control of barnyardgrass (Echinochloa crus-galli) and yellow nutsedge with only modest injury (8–25%) to soybean (Glycine max). A similar compound containing a bromine atom in the 5-position controlled yellow nutsedge greater than bentazon and affected soybean, sweet corn (Zea mays convar. saccharata var. rugosa), and rice (Oryza sativa) in a similar fashion to bentazon as well. The herbicidal sites of action targeted by these analogues of pyrazinamide and pyrazinoic acid are unknown, but it is hypothesized that they may be disrupting targets in the biosynthesis pathways of nicotinamide adenine dinucleotide (NAD) and/or ethylene.

Keywords: herbicide ; rice ; pyrazinamide ; pharmaceutical ; prodrug ; soybean ; sweet corn

Yuan, Gengyang ; Dhaynaut, Maeva ; Lan, Yu ; Guehl, Nicolas J. ; Huynh, Dalena ; Iyengar, Suhasini M. , et al.

Abstract: Metabotropic glutamate receptor 2 (mGluR2) is a therapeutic target for several neuropsychiatric disorders. An mGluR2 function in etiology could be unveiled by positron emission tomography (PET). In this regard, 5-(2-fluoro-4-[11C]methoxyphenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine-7-carboxamide ([11C]13, [11C]mG2N001), a potent negative allosteric modulator (NAM), was developed to support this endeavor. [11C]13 was synthesized via the O-[11C]methylation of phenol 24 with a high molar activity of 212 ± 76 GBq/μmol (n = 5) and excellent radiochemical purity (>99%). PET imaging of [11C]13 in rats demonstrated its superior brain heterogeneity and reduced accumulation with pretreatment of mGluR2 NAMs, VU6001966 (9) and MNI-137 (26), the extent of which revealed a time-dependent drug effect of the blocking agents. In a nonhuman primate, [11C]13 selectively accumulated in mGluR2-rich regions and resulted in high-contrast brain images. Therefore, [11C]13 is a potential candidate for translational PET imaging of the mGluR2 function.

Hegde, Pooja V. ; Aragaw, Wassihun W. ; Cole, Malcolm S. ; Jachak, Gorakhnath ; Ragunathan, Priya ; Sharma, Sachin , et al.

Abstract: Tuberculosis (TB) remains a leading cause of infectious disease-related mortality and morbidity. Pyrazinamide (PZA) is a critical component of the first-line TB treatment regimen because of its sterilizing activity against non-replicating Mycobacterium tuberculosis (Mtb), but its mechanism of action has remained enigmatic. PZA is a prodrug converted by pyrazinamidase encoded by pncA within Mtb to the active moiety, pyrazinoic acid (POA) and PZA resistance is caused by loss-of-function mutations to pyrazinamidase. We have recently shown that POA induces targeted protein degradation of the enzyme PanD, a crucial component of the CoA biosynthetic pathway essential in Mtb. Based on the newly identified mechanism of action of POA, along with the crystal structure of PanD bound to POA, we designed several POA analogs using structure for interpretation to improve potency and overcome PZA resistance. We prepared and tested ring and carboxylic acid bioisosteres as well as 3, 5, 6 substitutions on the ring to study the structure activity relationships of the POA scaffold. All the analogs were evaluated for their whole cell antimycobacterial activity, and a few representative mols. were evaluated for their binding affinity, towards PanD, through isothermal titration calorimetry. We report that analogs with ring and carboxylic acid bioisosteres did not significantly enhance the antimicrobial activity, whereas the alkylamino-group substitutions at the 3 and 5 position of POA were found to be up to 5 to 10-fold more potent than POA. Further development and mechanistic anal. of these analogs may lead to a next generation POA analog for treating TB.

Keywords: Tuberculosis ; Pyrazinoic acid ; pyrazinamide

Alternative Products

Product Details of 5-Hydroxypyrazine-2-Carboxylic Acid

CAS No. :34604-60-9
Formula : C5H4N2O3
M.W : 140.10
SMILES Code : O=C(C1=CNC(C=N1)=O)O
MDL No. :MFCD11978170
InChI Key :CGQFCIHUUCMACC-UHFFFAOYSA-N
Pubchem ID :161825

Safety of 5-Hydroxypyrazine-2-Carboxylic Acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 5-Hydroxypyrazine-2-Carboxylic Acid

* 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 [ 34604-60-9 ]
  • Downstream synthetic route of [ 34604-60-9 ]

[ 34604-60-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 67-56-1 ]
  • [ 34604-60-9 ]
  • [ 13924-95-3 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: at -20℃; for 0.5 h;
Stage #2: for 2 h; Reflux
Preparation 405-Hvdroxy-pyrazine-2-carboxylic acid methyl esterThionyl chloride (152ml_, 2.08mol) was added dropwise at -20 °C to methanol (5L). After the addition was completed, the mixture was stirred at this temperature for 30 minutes. Then 5- hydroxy-pyrazine-2-carboxylic acid (100g, 714mmol) was added, and the mixture was heated at reflux for 2 hours. The reaction mixture was concentrated in vacuo, and the residue was recrystallised from methanol (400ml_) to give 71 g (464mmol) of the title compound in 65percent yield.
61% With hydrogenchloride In 1,4-dioxane; water at 60 - 80℃; for 4 h; (62a)
Methyl 5-hydroxypyrazine-2-carboxylate
Commercially available 5-hydroxypyrazine-2-carboxylic acid (1.00 g, 7.14 mmol) was dissolved in methanol (5 mL), and a 4N hydrochloric acid/dioxane solution (25 mL) was added, followed by stirring at 60°C for 1.5 hours and heating to reflux at 80°C for 2.5 hours.
The reaction solution was brought back to room temperature, the solvent was distilled off under reduced pressure, and ethyl acetate (20 mL) was added to the resulting residue to allow it to be suspended.
The resulting precipitate was filtered off, and washed with ethyl acetate, followed by vacuum drying, to afford the desired compound (673 mg, yield 61percent) as an orange-brown solid.
1H-NMR (CD3OD, 400 MHz): δ 3.31 (1H, s), 3.85 (3H, s), 8.00 (1H, d, J=1.2 Hz), 8.13 (1H, d, J=1.2 Hz).
References: [1] Patent: WO2013/14567, 2013, A1, . Location in patent: Page/Page column 80-81.
[2] Patent: EP2239253, 2010, A1, . Location in patent: Page/Page column 96.
[3] Patent: EP1452525, 2004, A1, . Location in patent: Page 15.
 

Historical Records

Categories