1100750-18-2 Usage
Description
3-nitro-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol, also known as PA-824 or P122500, is a reduction analog of the bioreactive drug with potent anti-tuberculosis properties. It is a compound derived from the tetrahydroimidazo[1,2-a]pyridine class, characterized by its nitro group and hydroxyl functional group. This molecule has shown significant promise in the development of new anti-tuberculosis drugs due to its unique mechanism of action and effectiveness against drug-resistant strains of Mycobacterium tuberculosis.
Uses
Used in Pharmaceutical Industry:
3-nitro-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol is used as an anti-tuberculosis agent for its ability to target and inhibit the growth of Mycobacterium tuberculosis, the bacterium responsible for tuberculosis. It is particularly effective against drug-resistant strains, making it a valuable asset in the fight against multi-drug resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB).
The compound works by inhibiting the enzyme mycolic acid synthase, which is essential for the synthesis of mycolic acids, a key component of the mycobacterial cell wall. By disrupting this process, 3-nitro-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol weakens the cell wall, leading to the death of the bacteria.
Additionally, 3-nitro-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol has been shown to have a unique activation mechanism, where it is reduced by the mycobacterial electron transport system to form a highly reactive nitro radical. This reactive species can cause damage to the bacterial cell, further contributing to its anti-tuberculosis activity.
Check Digit Verification of cas no
The CAS Registry Mumber 1100750-18-2 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,1,0,0,7,5 and 0 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1100750-18:
(9*1)+(8*1)+(7*0)+(6*0)+(5*7)+(4*5)+(3*0)+(2*1)+(1*8)=82
82 % 10 = 2
So 1100750-18-2 is a valid CAS Registry Number.
1100750-18-2Relevant articles and documents
Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl] oxy}- 6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)
Thompson, Andrew M.,Blaser, Adrian,Anderson, Robert F.,Shinde, Sujata S.,Franzblau, Scott G.,Ma, Zhenkun,Denny, William A.,Palmer, Brian D.
supporting information; experimental part, p. 637 - 645 (2009/12/01)
The nitroimidazooxazine S-1 (PA-824) is a new class of bioreductive drug for tuberculosis. A series of related bicyclic nitroheterocycles was synthesized, designed to have a wide range of one-electron reduction potentials E(1) (from -570 to -338 mV, compared with -534 mV for S-1). The observed E(1) values closely correlated with the om values of the heteroatom at the 4/8-position of the adjacent six-membered ring. Although the compounds spanned a range of E(1) values around that of S-1, only the nitroimidazothiazines showed significant antitubercular activity (at a similar level of potency), suggesting that E(1) is not the main driver of efficacy. Furthermore, there was a correlation between activity and the formation of imidazole ring-reduced products at the two-electron level, pointing to the potential importance of this reduction pathway, which is determined by the nature of the substituent at the 2-position of the 4-nitroimidazole ring.
