158407-04-6 Usage
Description
4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals and chemicals. It is characterized by its molecular structure, which includes a bromomethyl group, a piperidine ring, a carboxylic acid group, and a tert-butyl ester group. These functional groups make it a versatile building block for the development of new compounds with potential applications in the pharmaceutical and chemical industries.
Uses
Used in Organic Synthesis:
4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is used as an organic synthesis intermediate for the creation of various chemical compounds. Its unique structure allows for further functionalization and modification, enabling the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is used as a pharmaceutical intermediate. It plays a vital role in the development of new drugs, particularly those targeting the central nervous system, as it can be incorporated into the molecular structure of potential therapeutic agents. Its presence in the final drug molecule can contribute to the drug's efficacy, safety, and pharmacokinetic properties.
Used in Laboratory Research and Development:
4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is also utilized in laboratory research and development processes. Researchers use this compound to explore its potential applications in various fields, such as medicinal chemistry, drug design, and chemical biology. Through these studies, scientists can gain a deeper understanding of the compound's properties and how it can be harnessed for the development of new drugs and chemicals.
Used in Chemical Production Process:
In the chemical production process, 4-BROMOMETHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is employed as a key component in the synthesis of various chemicals. Its versatility and reactivity make it an essential building block for the production of a wide range of chemical products, including specialty chemicals, agrochemicals, and materials for various industrial applications.
Synthesis
4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester. 4-N-Boc-piperidine-methanol (200 mg, 0.93 mmol) was dissolved in diethyl ether (9 mL) and carbon tetrabromide (370 mg, 1.1 mmol) and PPh3 (292 mg, 1.1 mmol) were added at rt. The reaction was allowed to stir for 18 h at rt and filtered over a pad of celite. The filtrate was concentrated and purified by flash chromatography (hexane/EtOAc, 1:0 → 4:1) to give the title compound. Yield 55 mg. 1 (400 MHz, DMSO-d6) δ ppm 4.02-3.98 (m, 2 H), 3.47 (d, 2 H), 2.78-2.65 (m, 2 H), 1.89-1.74 (m, 3 H), 1.45 (s, 9 H), 1.12-0.98 (m, 2 H).
Check Digit Verification of cas no
The CAS Registry Mumber 158407-04-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,8,4,0 and 7 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 158407-04:
(8*1)+(7*5)+(6*8)+(5*4)+(4*0)+(3*7)+(2*0)+(1*4)=136
136 % 10 = 6
So 158407-04-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H20BrNO2/c1-11(2,3)15-10(14)13-6-4-9(8-12)5-7-13/h9H,4-8H2,1-3H3
158407-04-6Relevant articles and documents
Structural requirements for TLR7-selective signaling by 9-(4-piperidinylalkyl)-8-oxoadenine derivatives
Bazin, Hélène G.,Li, Yufeng,Khalaf, Juhienah K.,Mwakwari, Sandra,Livesay, Mark T.,Evans, Jay T.,Johnson, David A.
, p. 1318 - 1323 (2015)
We report the synthesis and biological evaluation of a new series of 8-oxoadenines substituted at the 9-position with a 4-piperidinylalkyl moiety. In vitro evaluation of the piperidinyl-substituted oxoadenines 3a-g in human TLR7- or TLR8-transfected HEK293 cells and in human PBMCs indicated that TLR7/8 selectivity/potency and cytokine induction can be modulated by varying the length of the alkyl linker. Oxoadenine 3f containing a 5-carbon linker was found to be the most potent TLR7 agonist and IFNα inducer in the series whereas 3b possessing a 1-carbon linker was the most potent TLR8 agonist.
Identification of 2,4-Disubstituted Imidazopyridines as Hemozoin Formation Inhibitors with Fast-Killing Kinetics and in Vivo Efficacy in the Plasmodium falciparum NSG Mouse Model
Horatscheck, André,Andrijevic, Ana,Nchinda, Aloysius T.,Le Manach, Claire,Paquet, Tanya,Khonde, Lutete Peguy,Dam, Jean,Pawar, Kailash,Taylor, Dale,Lawrence, Nina,Brunschwig, Christel,Gibhard, Liezl,Njoroge, Mathew,Reader, Janette,Van Der Watt, Mari?tte,Wicht, Kathryn,De Sousa, Ana Carolina C.,Okombo, John,Maepa, Keletso,Egan, Timothy J.,Birkholtz, Lyn-Marie,Basarab, Gregory S.,Wittlin, Sergio,Fish, Paul V.,Street, Leslie J.,Duffy, James,Chibale, Kelly
supporting information, p. 13013 - 13030 (2020/11/13)
A series of 2,4-disubstituted imidazopyridines, originating from a SoftFocus Kinase library, was identified from a high throughput phenotypic screen against the human malaria parasite Plasmodium falciparum. Hit compounds showed moderate asexual blood stage activity. During lead optimization, several issues were flagged such as cross-resistance against the multidrug-resistant K1 strain, in vitro cytotoxicity, and cardiotoxicity and were addressed through structure-Activity and structure-property relationship studies. Pharmacokinetic properties were assessed in mice for compounds showing desirable in vitro activity, a selectivity window over cytotoxicity, and microsomal metabolic stability. Frontrunner compound 37 showed good exposure in mice combined with good in vitro activity against the malaria parasite, which translated into in vivo efficacy in the P. falciparum NOD-scid IL-2Rnull (NSG) mouse model. Preliminary mechanistic studies suggest inhibition of hemozoin formation as a contributing mode of action.
Compound with dual inhibitory activity TDO, IDOO1 and application of compound for treating neurodegenerative disease (by machine translation)
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Paragraph 0149; 0209-0210; 0213-0214, (2020/10/06)
The present invention provides a compound of formula I, or a pharmaceutically acceptable salt thereof, or a solvate thereof, which can selectively inhibit TDO, IDOO1, which has a significant inhibitory effect on TDO and/or IDOO1. In addition, the prepared compound has a remarkable anti-tumor effect, has a certain treatment effect on's disease and's disease, and has a good application prospect in the field of medicine preparation. (by machine translation)
