Category: 31253-08-4

Povie, Guillaume published the artcileRadical chain repair: The hydroalkylation of polysubstituted unactivated alkenes, COA of Formula: C5H9IO2, the publication is Science Advances (2018), 4(7), eaat6031, database is CAplus and MEDLINE.

The concept of repair is widely used by nature to heal mols. such as proteins, lipids, sugars, and DNA that are damaged by hydrogen atom abstraction resulting from oxidative stress. We show that this strategy, rather undocumented in the field of synthetic organic chem., can be used in a radical chain reaction to enable notoriously intractable transformations. By overcoming the radical chain inhibitor properties of substituted alkenes, the radical-mediated hydroalkylation of mono-, di-, tri-, and even tetrasubstituted unactivated olefins could be performed under mild conditions. With a remarkable functional group tolerance, this reaction provides a general coupling method for the derivatization of olefin-containing natural products.

Science Advances published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, COA of Formula: C5H9IO2.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Huang, Qi published the artcileA Giese reaction for electron-rich alkenes, Recommanded Product: Ethyl 2-Iodopropionate, the publication is Chemical Science (2021), 12(6), 2225-2230, database is CAplus and MEDLINE.

A general method for the hydroalkylation of electron-rich terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of triethylborane acting as a chain transfer reagent and 4-tert-butylcatechol (TBC) as a source of hydrogen atom. The efficacy of the reaction is best explained by very favorable polar effects supporting the chain process and minimizing undesired polar reactions. The stereoselective hydroalkylation of chiral N-(alk-1-en-1-yl)oxazolidin-2-ones takes place with good to excellent diastereocontrol.

Chemical Science published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Recommanded Product: Ethyl 2-Iodopropionate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Hwang, Jimin published the artcileOptimization of peptide-based inhibitors targeting the HtrA serine protease in Chlamydia: Design, synthesis and biological evaluation of pyridone-based and N-capping group-modified analogs, Formula: C5H9IO2, the publication is European Journal of Medicinal Chemistry (2021), 113692, database is CAplus and MEDLINE.

The obligate intracellular bacterium Chlamydia trachomatis (C. trachomatis) is responsible for the most common bacterial sexually transmitted infection and is the leading cause of preventable blindness, representing a major global health burden. While C. trachomatis infection is currently treatable with broad-spectrum antibiotics, there would be many benefits of a chlamydia-specific therapy. Previously, we have identified a small-mol. lead compound JO146 [Boc-Val-Pro-Val^P(OPh)₂] targeting the bacterial serine protease HtrA, which is essential in bacterial replication, virulence and survival, particularly under stress conditions. JO146 is highly efficacious in attenuating infectivity of both human (C. trachomatis) as well as koala (C. pecorum) species in vitro and in vivo, without host cell toxicity. Herein, we present our continuing efforts on optimizing JO146 by modifying the N-capping group as well as replacing the parent peptide structure with the 2-pyridone scaffold at P3/P2. The drug optimization process was guided by mol. modeling, enzyme and cell-based assays. Compound (I) (Cbz = benzyloxycarbonyl) from the pyridone series showed improved inhibitory activity against CtHtrA by 5-fold and selectivity over human neutrophil elastase (HNE) by 109-fold compared to JO146, indicating that 2-pyridone is a suitable bioisostere of the P3/P2 amide/proline for developing CtHtrA inhibitors. Most pyridone-based inhibitors showed superior anti-chlamydial potency to JO146 especially at lower doses (25 and 50μM) in C. trachomatis and C. pecorum cell culture assays. Modifications of the N-capping group of the peptidyl inhibitors did not have much influence on the anti-chlamydial activities, providing opportunities for more versatile alterations and future optimization. In summary, we present 2-pyridone based analogs as a new generation of non-peptidic CtHtrA inhibitors, which hold better promise as anti-chlamydial drug candidates.

European Journal of Medicinal Chemistry published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Formula: C5H9IO2.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Poli, Rinaldo published the artcileNew mechanistic insights into ATRP using molybdenum coordination compounds, Name: Ethyl 2-Iodopropionate, the publication is Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) (2005), 46(2), 305-306, database is CAplus.

Atom transfer radical polymerization (ATPR) of Me acrylate (MA) using the same halogen on both the Mo complex catalyst (CpMoX₂(ⁱPr₂dad); X = Cl or iodine; dad = diazadiene) and the initiator (MeCHYCO₂Et; Y = Cl or iodine) was unsuccessful when the halogen was Cl and no cocatalyst was present. However, the polymerization occurred smoothly in the presence of the cocatalyst Al(OPrⁱ)₃. M_n grew linearly with the conversion, although the polydispersity index was relatively high (ca. 1.5). The apparent rate constant increased by a factor of ca. 10 on changing the initiator from MeCHClCO₂Et to MeCHICO₂Et. The initiator efficiency factor, f, was 0.37 when using the chloride initiator, the lowest value observed so far. In the case of the fully iodine-based system, the polymerization was pseudo-living both with and without Al(OPrⁱ)₃. Thus, the ATRP of MA os accelerated by replacing Cl by iodine in the Mo catalyst (by a factor of ca. 5) and f is unity for this system. Finally, investigations of the stable free radical polymerization (SFRP) of styrene and MA revealed that irreversible radical trapping occurred. The low initiator efficiency factor in ATRP may be explained rather easily, and indeed must be expected, each time that the ATRP catalyst is also capable of trapping irreversibly the active radical.

Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Name: Ethyl 2-Iodopropionate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Poli, Rinaldo published the artcileAn experimental and computational study on the effect of Al(OiPr)₃ on atom-transfer radical polymerization and on the catalyst-dormant-chain halogen exchange, Quality Control of 31253-08-4, the publication is Chemistry – A European Journal (2005), 11(8), 2537-2548, database is CAplus and MEDLINE.

Compound Al(OiPr)₃ is shown to catalyze the halide-exchange process leading from [Mo(Cp)Cl₂(iPrN=CH-CH=NiPr)] and CH₃CH-(X)COOEt (X=Br, I) to the mixed-halide complexes [Mo(Cp)ClX(iPrN=CH-CH=NiPr)]. No significant acceleration is observed for the related exchange between [MoX₃(PMe₃)₃] (X=Cl, I) and PhCH(Br)CH₃, by analogy to a previous report dealing with the Ru^II complex [RuCl₂(PPh₃)₃]. A DFT computation study, carried out on the model complexes [Mo(Cp)Cl₂(PH₃)₂], [MoCl₃(PH₃)₃], and [RuCl₂(PH₃)₃], and on the model initiators CH₃CH(Cl)COOCH₃, CH₃Cl, and CH₃Br, reveals that the 16-electron Ru^II complex is able to coordinate the organic halide RX in a slightly exothermic process to yield saturated, diamagnetic [RuCl₂(PH₃)₃(RX)] adducts. The 15-electron [MoCl₃(PH₃)₃] complex is equally capable of forming an adduct, i.e., the 17-electron [MoCl₃(PH₃)₃(CH₃Cl)] complex with a spin doublet configuration, although the process is endothermic, because it requires an energetically costly electron-pairing process. The interaction between the 17-electron [Mo(Cp)Cl₂(PH₃)₂] complex and CH₃Cl, is repulsive and does not lead to a stable 19-electron adduct. The [RuCl₂(PH₃)₃(CH₃X)] system leads to an isomeric complex [RuClX(PH₃)₃(CH₃Cl)] by internal nucleophilic substitution at the carbon atom. The transition state of this process for X=Cl (degenerate exchange) is located at lower energy than the transition state required for halogen-atom transfer leading to [RuCl₃(PH₃)₃] and the free radical CH₃. On the basis of these results, the uncatalyzed halide exchange is interpreted as the result of a competitive S_Ni process, whose feasibility depends on the electronic configuration of the transition-metal complex. The catalytic action of Al(OiPr)₃ on atom-transfer radical polymerization (and on halide exchange for the 17-electron half-sandwich Mo^III complex) results from a more favorable Lewis acid-base interaction with the oxidized metal complex, in which the transferred halogen atom is bound to a more electro-pos. element. This conclusion derives from DFT studies of the model [Al(OCH₃)₃]_n (n=1,2,3,4) compounds, and on the interaction of Al(OCH₃)₃ with CH₃Cl and with the [Mo(Cp)Cl₃(PH₃)₂] and [RuCl₃(PH₃)₃] complexes.

Chemistry – A European Journal published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Quality Control of 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Muanprasat, Chatchai published the artcileDiscovery of glycine hydrazide pore-occluding CFTR inhibitors: mechanism, structure-activity analysis, and in vivo efficacy, Related Products of iodides-buliding-blocks, the publication is Journal of General Physiology (2004), 124(2), 125-137, database is CAplus and MEDLINE.

The cystic fibrosis transmembrane conductance regulator (CFTR) protein is a cAMP-regulated epithelial Cl^– channel that, when defective, causes cystic fibrosis. Screening of a collection of 100,000 diverse small mols. revealed four novel chem. classes of CFTR inhibitors with K_i < 10 μM, one of which (glycine hydrazides) had many active structural analogs. Anal. of a series of synthesized glycine hydrazide analogs revealed maximal inhibitory potency for N-(2-naphthalenyl) and 3,5-dibromo-2,4-dihydroxyphenyl substituents. The compound N-(2-naphthalenyl)-[(3,5-dibromo-2,4-dihydroxyphenyl)methylene]glycine hydrazide (GlyH-101) reversibly inhibited CFTR Cl^– conductance in <1 min. Whole-cell current measurements revealed voltage-dependent CFTR block by GlyH-101 with strong inward rectification, producing an increase in apparent inhibitory constant K_i from 1.4 μM at + 60 mV to 5.6 μM at – 60 mV. Apparent potency was reduced by lowering extracellular Cl^– concentration Patch-clamp experiments indicated fast channel closures within bursts of channel openings, reducing mean channel open time from 264 to 13 ms (-60 mV holding potential, 5 μM GlyH-101). GlyH-101 inhibitory potency was independent of pH from 6.5-8.0, where it exists predominantly as a monovalent anion with solubility ∼1 mM in water. Topical GlyH-101 (10 μM) in mice rapidly and reversibly inhibited forskolin-induced hyperpolarization in nasal potential differences. In a closed-loop model of cholera, intraluminal GlyH-101 (2.5 μg) reduced by ∼80% cholera toxin-induced intestinal fluid secretion. Compared with the thiazolidinone CFTR inhibitor CFTR_inh-172, GlyH-101 has substantially greater water solubility and rapidity of action, and a novel inhibition mechanism involving occlusion near the external pore entrance. Glycine hydrazides may be useful as probes of CFTR pore structure, in creating animal models of CF, and as antidiarrheals in enterotoxic-mediated secretory diarrheas.

Journal of General Physiology published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Related Products of iodides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Loiseau, Francois published the artcileRadical Couplings as Key Steps for the Preparation of Derivatives of Nonactic Acid, Application In Synthesis of 31253-08-4, the publication is Monatshefte fuer Chemie (2007), 138(2), 121-129, database is CAplus.

Free radical couplings from furan, as cheap starting material, were studied in view of developing a rapid strategy en route to the synthesis of derivatives of nonactin. The chain containing the alc. function was introduced in one or two steps in 86% yield. For the introduction of the second chain with the ester function two different coupling methods were tested. Starting from the advanced intermediates obtained by this method, nonactin analogs, such s I (R = CMe₃, CH₂Me), were prepared by catalytic hydrogenation of the furan ring.

Monatshefte fuer Chemie published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Application In Synthesis of 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Nugent, Jeremy published the artcileSynthesis of All-Carbon Disubstituted Bicyclo[1.1.1]pentanes by Iron-Catalyzed Kumada Cross-Coupling, Category: iodides-buliding-blocks, the publication is Angewandte Chemie, International Edition (2020), 59(29), 11866-11870, database is CAplus and MEDLINE.

1,3-Disubstituted bicyclo[1.1.1]pentanes (BCPs) are important motifs in drug design as surrogates for p-substituted arenes and alkynes. Access to all-carbon disubstituted BCPs via cross-coupling has to date been limited to use of the BCP as the organometallic component, which restricts scope due to the harsh conditions typically required for the synthesis of metalated BCPs. Here the authors report a general method to access 1,3-C-disubstituted BCPs from 1-iodo-bicyclo[1.1.1]pentanes (iodo-BCPs) by direct iron-catalyzed cross-coupling with aryl and heteroaryl Grignard reagents. This chem. represents the first general use of iodo-BCPs as electrophiles in cross-coupling, and the first Kumada coupling of tertiary iodides. Benefiting from short reaction times, mild conditions, and broad scope of the coupling partners, it enables the synthesis of a wide range of 1,3-C-disubstituted BCPs including various drug analogs.

Angewandte Chemie, International Edition published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Category: iodides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Tsuboi, Sadao published the artcileNew synthesis of (±)-menthofuran, Recommanded Product: Ethyl 2-Iodopropionate, the publication is Journal of Organic Chemistry (1980), 45(8), 1517-20, database is CAplus.

(±)-Menthofuran [(±)-I] was prepared in 3 steps from Et 4-methyl- 2-oxo-1-cyclohexanecarboxylate (II) in a reasonable overall yield. Reaction of II with MeCHICO₂Et gave Et 2-(1-ethoxycarbonyl-4-methyl-2-oxocyclohexyl)propionate, which was converted directly to 3,6-dimethyl-2,4,5,6,7,7a-hexahydro-2-benzofuranone (III) by refluxing with concentrate HCl; reduction with LiAlH₄-Me₂CHOH at -60 to -50° gave (±)-I. The reduction of III at room temperature gave 2-(4-methyl-1-cyclohexenyl)-1,2-propanediol.

Journal of Organic Chemistry published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C17H14F3N3O2S, Recommanded Product: Ethyl 2-Iodopropionate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

McCaffery, E. L. published the artcilePolymetallophilic organic compounds. III. Competitive intramolecular Grignard coupling reactions, Application In Synthesis of 31253-08-4, the publication is Journal of Organometallic Chemistry (1972), 44(2), 227-31, database is CAplus.

Ring formation via an intramol. Grignard coupling reaction of trihalo alkanes is presented. 2-Methyl-2-(chloromethyl)-1,5-dichloropentane was prepared and treated with two equivalent Mg in THF to study the possible ring formation through 1,5 and/or 1,3 coupling reactions. A 1,3 Grignard coupling reaction was shown to occur preferentially, and a cyclopropane derivative I was formed. A 1,5 coupling reaction could not be realized under the prevailing reaction conditions. A diradical mechanism for the Grignard coupling reaction is proposed to account for the behavior of this compound and other similar polymetallophilic systems in their reaction with Mg.

Journal of Organometallic Chemistry published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C5H9IO2, Application In Synthesis of 31253-08-4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com