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Chemistry
Organic Building Blocks
Iodides
1-Iodoethyl isopropyl carbonate
Chemistry
Organic Building Blocks
Iodides
Aliphatic Chain Hydrocarbons

[ CAS No. 84089-73-6 ] 1-Iodoethyl isopropyl carbonate

Cat. No.: A426225
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Chemical Structure| 84089-73-6
Chemical Structure| 84089-73-6
 Structure of 84089-73-6 * Storage: Keep in dark place,Inert atmosphere,2-8°C
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
95% 1g $1020.00 Inquiry Inquiry

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* Storage: Keep in dark place,Inert atmosphere,2-8°C

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 84089-73-6 ]

COA NMR CNMR HPLC LC-MS

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Product Citations

Product Citations

Pooja V. Hegde ; Michael D. Howe ; Matthew D. Zimmerman , et al. DOI: PubMed ID:

Abstract: Tuberculosis (TB) is one of the world's most deadly infectious diseases resulting in nearly 1.3 million deaths annually and infecting nearly one-quarter of the population. para-Aminosalicylic acid (PAS), an important second-line agent for treating drug-resistant Mycobacterium tuberculosis, has moderate bioavailability and rapid clearance that necessitate high daily doses of up to 12 g per day, which in turn causes severe gastrointestinal disturbances presumably by disruption of gut microbiota and host epithelial cells. We first synthesized a series of alkyl, acyloxy and alkyloxycarbonyloxyalkyl ester prodrugs to increase the oral bioavailability and thereby prevent intestinal accumulation as well as undesirable bioactivation by the gut microbiome to non-natural folate species that exhibit cytotoxicity. The pivoxyl prodrug of PAS was superior to all of the prodrugs examined and showed nearly quantitative absorption. While the conceptually simple prodrug approach improved the oral bioavailability of PAS, it did not address the intrinsic rapid clearance of PAS mediated by N-acetyltransferase-1 (NAT-1). Thus, we next modified the PAS scaffold to reduce NAT-1 catalyzed inactivation by introduction of groups to sterically block N-acetylation and fluorination of the aryl ring of PAS to attenuate N-acetylation by electronically deactivating the para-amino group. Among the mono-fluorinated analogs prepared, 5-fluoro-PAS, exhibited the best activity and an 11-fold decreased rate of inactivation by NAT-1 that translated to a 5-fold improved exposure as measured by area-under-the-curve (AUC) following oral dosing to CD-1 mice. The pivoxyl prodrug and fluorination at the 5-position of PAS address the primary limitations of PAS and have the potential to revitalize this second-line TB drug.

Keywords: Tuberculosis ; para-Aminosalicylic acid (PAS) ; Prodrug ; Fluorination ; Metabolism ; N-acetyltransferase

Purchased from AmBeed: ; ; ; ; ; ; ; ; 75-07-0 ; ; ; ; ; 75-30-9 ; 3282-30-2 ; ; ;

Product Details of [ 84089-73-6 ]

CAS No. :84089-73-6 MDL No. :MFCD09031344
Formula : C6H11IO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 258.05 Pubchem ID :-
Synonyms :

Safety of [ 84089-73-6 ]

Signal Word:Danger Class:8(3)
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405 UN#:2920
Hazard Statements:H226-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 84089-73-6 ]

* 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 [ 84089-73-6 ]

[ 84089-73-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 84089-73-6 ]
  • [ 1397-89-3 ]
  • [ 1112349-89-9 ]
YieldReaction ConditionsOperation in experiment
8.3% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0℃; for 3h; Dissolving 461mg (0.5mmol) of amphotericin B in 3ml of DMF, cooling to 0C and adding 153mg of DBU, stirring for 5 minutes, then immediately adding 219mg (0.85mmol) of 1-iodoethyl isopropyl carbonate, and strongly stirring for 3 hours, using thin layer chromatography to trace the reaction, after the reaction almost finishes, adding 70ml ice water, stirring for 10 minutes and then standing for 2 hours, filtering and collecting, washing by 3mlx3 of water, dissolving the deep yellow solid in methanol, adding activated carbon to decolor, concentrating the filtrate under reduced pressure until solid is precipitated, cooling and standing overnight, filtering, using a little diluted methanol to wash twice, drying at 40C to give 43.6mg of yellow solid amphotericin B isopropoxycarbonyloxyethyl ester, with a yield of 8.3%. MS ES+: M+H 1054.15
8.3% Example 2; The preparation of amphotericin B isopropoxycarbonyloxyethyl ester; Dissolving 461 mg (0.5 mmol) of amphotericin B in 3 ml of DMF, cooling to 0 C. and adding 153 mg of DBU, stirring for 5 minutes, then immediately adding 219 mg (0.85 mmol) of 1-iodoethyl isopropyl carbonate, and strongly stirring for 3 hours, using thin layer chromatography to trace the reaction, after the reaction almost finishes, adding 70 ml ice water, stirring for 10 minutes and then standing for 2 hours, filtering and collecting, washing by 3 ml×3 of water, dissolving the deep yellow solid in methanol, adding activated carbon to decolor, concentrating the filtrate under reduced pressure until solid is precipitated, cooling and standing overnight, filtering, using a little diluted methanol to wash twice, drying at 40 C. to give 43.6 mg of yellow solid amphotericin B isopropoxycarbonyloxyethyl ester, with a yield of 8.3%.MS ES+: M+H 1054.15
Reference： [1]Patent: EP2174944,2010,A1 .Location in patent: Page/Page column 18
[2]Patent: US2010/210576,2010,A1 .Location in patent: Page/Page column 14
  • 2
  • [ 42017-89-0 ]
  • [ 84089-73-6 ]
  • [ 1319719-22-6 ]
Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5915 - 5926

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Technical Information

• Alkyl Halide Occurrence • General Reactivity • Heat of Combustion • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling
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