187235-08-1

Basic information

• Product Name: (S)-2-NITRO-6,7-DIHYDRO-5H-IMIDAZO[2,1-B][1,3]OXAZIN-6-OL
• Synonyms: (S)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol;（s）-2-nitro-6，7-dihydro-5H-imidazole[2,1-B][1,3]oxazin-6--ol;5H-Imidazo[2,1-b][1,3]oxazin-6-ol, 6,7-dihydro-2-nitro-, (6S)-;(6S)-2-nitro-5H,6H,7H-imidazo[2,1-b][1,3]oxazin-6-ol
• CAS NO: 187235-08-1
• Molecular Formula: C₆H₇N₃O₄
• Molecular Weight: 185.14
• Mol File: 187235-08-1.mol

Chemical Properties

• Boiling Point: 446.2°Cat760mmHg
• Flash Point: 223.7°C
• Appearance: /
• Density: 1.91g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.765
• Storage Temp.: 2-8°C
• Solubility: Chloroform, DCM, Methanol
• PKA: 13.21±0.20(Predicted)
• CAS DataBase Reference: (S)-2-NITRO-6,7-DIHYDRO-5H-IMIDAZO[2,1-B][1,3]OXAZIN-6-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-NITRO-6,7-DIHYDRO-5H-IMIDAZO[2,1-B][1,3]OXAZIN-6-OL(187235-08-1)
• EPA Substance Registry System: (S)-2-NITRO-6,7-DIHYDRO-5H-IMIDAZO[2,1-B][1,3]OXAZIN-6-OL(187235-08-1)

Safety Data

• Hazardous Substances Data: 187235-08-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-NITRO-6,7-DIHYDRO-5H-IMIDAZO[2,1-B][1,3]OXAZIN-6-OL is used as an intermediate in the synthesis of (S)-PA 824 (P122500), a novel anti-tuberculosis drug. (S)-2-NITRO-6,7-DIHYDRO-5H-IMIDAZO[2,1-B][1,3]OXAZIN-6-OL plays a crucial role in the development of new and effective treatments for tuberculosis, a disease that continues to be a major global health concern. The compound's unique structure and properties make it a valuable building block in the creation of innovative pharmaceuticals targeting tuberculosis.

InChI:InChI=1/C6H7N3O4/c10-4-1-8-2-5(9(11)12)7-6(8)13-3-4/h2,4,10H,1,3H2/t4-/m0/s1

Upstream product

• 187235-04-7 C₁₂H₂₂N₄O₆Si 
• 187235-06-9 (S)-2-nitro-6-(tetrahydro-pyran-2-yloxy)-6,7-dihydro-5H-imidazo[2,1-b]-[1,3]oxazine 

Downstream Products

• 1353754-01-4 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl methyl[4-(trifluoromethoxy)phenyl]carbamate 
• 187235-47-8 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl [4-(trifluoromethoxy)phenyl]carbamate 
• 1353754-81-0 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl (4-bromobenzyl)carbamate 
• 1353753-57-7 (6S)-2-nitro-6-{[3-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine 
• 187235-49-0 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl (4-bromophenyl)carbamate 
• 1353754-76-3 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl (3-iodophenyl)carbamate 
• 1353754-74-1 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl (3-bromophenyl)carbamate 
• 1353754-79-6 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl (4-iodophenyl)carbamate 
• 187235-52-5 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl [4-(trifluoromethoxy)benzyl]carbamate 
• 1353754-73-0 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl 4-{methyl[4-(trifluoromethoxy)benzyl]amino}piperidine-1-carboxylate 
• 1353754-71-8 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl (3S)-3-[4-(trifluoromethoxy)phenoxy]pyrrolidine-1-carboxylate 
• 1353754-70-7 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl {4-[6-(trifluoromethyl)pyridin-3-yl]benzyl}carbamate 
• 1353754-69-4 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl {[4'-(trifluoromethoxy)biphenyl-4-yl]methyl}carbamate 
• 1353754-68-3 (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl [(4'-fluorobiphenyl-4-yl)methyl]carbamate 

Relevant articles and documents

Synthesis method of PA-824

The invention relates to a synthesis method of PA-824, which belongs to the technical field of pharmaceutical chemical engineering. According to the synthesis method of PA-824 disclosed by the invention, LiOH is utilized to carry out deprotection on aliphatic silyl ether protecting groups under the condition of heating. The synthesis method of PA-824 disclosed by the invention avoids the use of tetraalkyl ammonium fluoride and acidic substances, is easy and convenient to operate, increases reaction yield and the purity of the target product, and is favorable for industrial production.

Novel lead generation of an anti-tuberculosis agent active against non-replicating mycobacteria: Exploring hybridization of pyrazinamide with multiple fragments

The key to shortening tuberculosis (TB) drug regimen lies in eliminating the reservoir of non-replicating persistent (NRP) Mycobacterium tuberculosis (Mtb). Pyrazinamide (PZA) is the only known drug used as part of a combination therapy that is believed to kill NRP Mtb and achieve sterilization. PZA is active only under low pH screening conditions. Screening and identification of NRP-active anti-TB compounds are severely limited because compounds are usually inactive under regular assay conditions. In an effort to design novel NRP-active anti-TB compounds, we used pyrazinamide as a core and hybridized it with the fragments derived from marketed drugs. One of these designs, compound 8, was a hybrid with fluoroquinolone. This compound exhibited >10 fold improvement in NRP activity under low pH condition as compared to pyrazinamide and a modest activity (0.8 log10 kill) under nutritionally starved NRP condition. Furthermore, compound 8 was active against fluoroquinolone-resistant strains and did not show any activity in a DNA supercoiling assay (gyrase inhibition), suggesting that its mechanism of action is not that of the parent fluoroquinolone. These results provide a novel avenue in the exploration of new chemotypes that are active against non-replicating Mtb.

Integration of solventless reaction in a multi-step process: Application to an efficient synthesis of PA-824

In order to improve redundant synthetic processes, the integration of a solventless reaction has proved to be useful for gaining high reaction mass efficiency (RME) as well as reducing the amount of solvents. This concept was applied to synthesis of PA-82

NITROIMIDAZOLE COMPOUNDS

The present invention relates to certain nitroimidazole compounds, which have interesting pharmaceutical properties. In particular, the compounds are useful in the treatment and/or prevention of infections such as those caused by Mycobacterium tuberculosis, Trypanosoma cruzi or Leishmania donovani. The invention also relates to pharmaceutical compositions containing the compounds, as well as processes for their preparation.

Process for preparing for imidazopyran derivatives

A novel process for preparing imidazopyran derivatives of the formula: wherein R1 is halogen atom, hydrogen atom, C1 to C3 alkyl group, aryl group, or aryl group substituted by C1 to C3 alkyl group, b