Month: February 2023

Application of Oppolzer’s sultam in the synthesis of cyclic α-amino acids and β-amino acids was written by Wozniak, D.;Szymanska, A.;Oldziej, S.;Lankiewicz, L.;Grzonka, Z.. And the article was included in Polish Journal of Chemistry in 2006.Product Details of 10297-05-9 This article mentions the following:

In this paper we describe the application of Oppolzer’s sultam as a chiral auxiliary for the synthesis of cyclic α- and β²-amino acids. The key step of the synthesis is stereoselective alkylation of sultam-derived glycine and β-alanine Schiff’s bases leading to diastereometrically pure products. Final compounds are obtained after mild acidic and then basic hydrolyzes of auxiliary groups and can be directly converted into N-tert-butoxycarbonyl- or N-fluorenylmethoxycarbonyl derivatives useful in peptide synthesis. In the case of substrates alkylated with dihaloalkanes spontaneous cyclization occurring during removal of the auxiliary groups yields cyclic α-amino acids (proline homologues) with reasonable yield and stereoselectivity. Theor. data explain the differences in tendency for cyclization between α- and β-amino acids. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Product Details of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Product Details of 10297-05-9

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Copper-assisted displacement reaction of nonactivated iodoarenes with arenesulfinates. Convenient alternative synthesis of unsymmetrical diaryl sulfones was written by Suzuki, Hitomi;Abe, Hajime. And the article was included in Tetrahedron Letters in 1995.Reference of 3268-21-1 This article mentions the following:

In the presence of CuI in hot DMF, a variety of functionalized iodoarenes ArI (Ar = Ph, 4-MeC₆H₄, C₆Me₅, 4-PhSC₆H₄, etc.) undergo nucleophilic displacement reaction with sodium arenesulfinates Ar’SO₂Na (Ar’ = Ph, 4-MeC₆H₄) to give the corresponding unsym. diaryl sulfones ArSO₂Ar’ in moderate to good yields. In the experiment, the researchers used many compounds, for example, 1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1Reference of 3268-21-1).

1,4-Diiodo-2,3,5,6-tetramethylbenzene (cas: 3268-21-1) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Reference of 3268-21-1

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Mild and efficient iodination of aromatic compounds with pyridine-iodine monochloride complex (PylCl) was written by Muathen, Hussni A.. And the article was included in Journal of Chemical Research, Synopses in 1994.Product Details of 20776-54-9 This article mentions the following:

A wide range of aromatic compounds (e.g., C₆H₆) have been effectively iodinated with a pyridine-iodine monochloride complex (I). Condensed polycyclic iodides, which are not readily obtained via direct iodination, can be prepared indirectly via their corresponding organomercurials in 1 step. Some benzoid and nonbenzoid heterocycles (e.g., indole) are iodinated with I. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9Product Details of 20776-54-9).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Product Details of 20776-54-9

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Defining the Mechanism of Action and Enzymatic Selectivity of Psammaplin A against Its Epigenetic Targets was written by Baud, Matthias G. J.;Leiser, Thomas;Haus, Patricia;Samlal, Sharon;Wong, Ai Ching;Wood, Robert J.;Petrucci, Vanessa;Gunaratnam, Mekala;Hughes, Siobhan M.;Buluwela, Lakjaya;Turlais, Fabrice;Neidle, Stephen;Meyer-Almes, Franz-Josef;White, Andrew J. P.;Fuchter, Matthew J.. And the article was included in Journal of Medicinal Chemistry in 2012.COA of Formula: C8H7IO2 This article mentions the following:

Psammaplin A (11c) is a marine metabolite previously reported to be a potent inhibitor of two classes of epigenetic enzymes: histone deacetylases and DNA methyltransferases. The design and synthesis of a focused library based on the psammaplin A core has been carried out to probe the mol. features of this mol. responsible for its activity. By direct in vitro assay of the free thiol generated upon reduction of the dimeric psammaplin scaffold, we have unambiguously demonstrated that 11c functions as a natural prodrug, with the reduced form being highly potent against HDAC1 in vitro (IC₅₀ 0.9 nM). Furthermore, we have shown it to have high isoform selectivity, being 360-fold selective for HDAC1 over HDAC6 and more than 1000-fold less potent against HDAC7 and HDAC8. SAR around our focused library revealed a number of features, most notably the oxime functionality to be important to this selectivity. Many of the compounds show significant cytotoxicity in A549, MCF7, and W138 cells, with the SAR of cytotoxicity correlating to HDAC inhibition. Furthermore, compound treatment causes upregulation of histone acetylation but little effect on tubulin acetylation. Finally, we have found no evidence for 11c functioning as a DNMT inhibitor. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6COA of Formula: C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.COA of Formula: C8H7IO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Transition-metal-free decarboxylative iodination: New routes for decarboxylative oxidative cross-couplings was written by Perry, Gregory J. P.;Quibell, Jacob M.;Panigrahi, Adyasha;Larrosa, Igor. And the article was included in Journal of the American Chemical Society in 2017.Product Details of 36748-88-6 This article mentions the following:

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional mols., and efficient methods for their synthesis from chem. feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I₂. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I₂ as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Product Details of 36748-88-6).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Product Details of 36748-88-6

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A versatile synthesis of long-wavelength-excitable BODIPY dyes from readily modifiable cyclopenta[2,1-b:3,4-b’]dithiophenes was written by Sutter, Alexandra;Ziessel, Raymond. And the article was included in Synlett in 2014.Related Products of 474416-61-0 This article mentions the following:

Knoevenagel condensation of a simple methylated borondipyrromethene (Bodipy) with 4,4′-dihexyl-4H-cyclopenta-[2,1-b:3,4-b’]dithiophenes functionalized at one end by a triphenylamine residue and at the other by a carbaldehyde fragment leads to novel dye species. These bisvinylic derivatives exhibit pronounced absorption in the visible range extending above 850 nm. Addition of other Bodipy units by coupling to a central iodophenyl entity enables filling of the gaps in absorption of the pivotal starting material. Efficient cascade energy transfer between the Bodipys is facilitated by spectral overlap between the energy donor and the energy acceptor. All photons between 350 nm and 750 nm are channeled to the distyryl centers which emit at 864 nm. In the experiment, the researchers used many compounds, for example, Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0Related Products of 474416-61-0).

Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Related Products of 474416-61-0

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis, biological evaluation and molecular modeling of a novel series of 7-azaindole based tri-heterocyclic compounds as potent CDK2/Cyclin E inhibitors was written by Baltus, Christine B.;Jorda, Radek;Marot, Christophe;Berka, Karel;Bazgier, Vaclav;Krystof, Vladimir;Prie, Gildas;Viaud-Massuard, Marie-Claude. And the article was included in European Journal of Medicinal Chemistry in 2016.Electric Literature of C7H5IN2 This article mentions the following:

From four mols., inspired by the structural features of fascaplysin, with an interesting potential to inhibit cyclin-dependent kinases (CDKs), we designed a new series of tri-heterocyclic derivatives based on 1H-pyrrolo[2,3-b]pyridine (7-azaindole) and triazole heterocycles. Using a Huisgen type [3 + 2] cycloaddition as the convergent key step, 24 derivatives were synthesized and their biol. activities were evaluated. Comparative mol. field anal. (CoMFA), based on three-dimensional quant. structure-activity relationship (3D-QSAR) studies, was conducted on a series of 30 compounds from the literature with high to low known inhibitory activity towards CDK2/cyclin E and was validated by a test set of 5 compounds giving satisfactory predictive r² value of 0.92. Remarkably, it also gave a good prediction of pIC₅₀ for our tri-heterocyclic series which reinforce the validation of this model for the pIC₅₀ prediction of external set compounds The most promising compound, I, showed a micro-molar range inhibitory activity against CDK2/cyclin E and also an antiproliferative and proapoptotic activity against a panel of cancer cell lines. In the experiment, the researchers used many compounds, for example, 2-Iodo-1H-pyrrolo[2,3-b]pyridine (cas: 1227270-32-7Electric Literature of C7H5IN2).

2-Iodo-1H-pyrrolo[2,3-b]pyridine (cas: 1227270-32-7) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Electric Literature of C7H5IN2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis of Substituted Indole from 2-Aminobenzaldehyde through [1,2]-Aryl Shift was written by Levesque, Patrick;Fournier, Pierre-Andre. And the article was included in Journal of Organic Chemistry in 2010.Synthetic Route of C7H6INO2 This article mentions the following:

A mild, efficient, and simple method for the synthesis of 3-ethoxycarbonylindoles has been developed. Addition of Et diazoacetate (EDA) to 2-aminobenzaldehydes cleanly affords the indole core. E.g., addition of Et diazoacetate to 2-(benzylamino)-6-fluorobenzaldehyde (I) in presence of BF₃.OEt₂ gave 85% Et 1-benzyl-4-fluoroindole-3-carboxylate (II). As opposed to other common approaches for the synthesis of indole, this method displays both excellent functional group tolerance and perfect regiochem. control. This allowed the synthesis of a variety of useful indole building blocks from 2-aminobenzaldehydes derived from readily available anthranilic acids. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9Synthetic Route of C7H6INO2).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Synthetic Route of C7H6INO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Molecular configuration of polynuclear aromatic compounds. IV. 6,6′-Dichlorodiphenic acid; its synthesis and resolution into optically active components was written by Christie, G. H.;James, C. W.;Kenner, James. And the article was included in Journal of the Chemical Society, Transactions in 1923.Recommanded Product: 123278-03-5 This article mentions the following:

2-Iodoaceto-m-toluidide is oxidized by KMnO₄ in boiling H₂O containing MgSO₄ to 2-iodo-3-acetylaminobenzoic acid, m. 199°. Hydrolysis with concentrated HCl gives the HCl salt of 2-iodo-3-aminobenzoic acid, m. 262-3°. 3-Chloro-2-iodobenzoic acid, m. 137-8°; Me ester, b₂₈ 182°; Et ester, b₁₅ 175°. The Me ester and Cu powder, heated 1 hr. at 230-40°, give 6,6′-dichlorodiphenic acid, m. 288°, as the Me ester, m. 156°. Et ester, m. 103-4°. Repeated fractional crystallization of the mixture of salts from 2 g. acid and 6 g. hydrated brucine gave 2.3 g. of brucine 1-6,6′-dichlorodiphenate, C₆₀H₆₀O₁₂N₄Cl₂.3H₂O, m. 235°; and is the less soluble of the 2 salts. [α]_D¹⁵ 1.97 (CHCl₃, c 1.23%). The d-salt, obtained in a yield of 1.35 g., m. 163° (decomposition), is the more soluble and has [α]_D¹⁵ -58.62° (CHCl₃, c 1.16%). This salt crystallines with 1.5 H₂O. d-6,6′-Dichlorodiphenic acid, m. 259°. A 0.69% solution of the Na salt showed [α]_D¹⁵ -20.18°. The l-acid m. 259°; a 1.01% aqueous solution of the Na salt showed [α]_D¹⁵ 21.43°. These results confirm the correctness of the assumption that the cause of the stereoisomerism of the various nitrodiphenic acids previously investigated is not to be sought in any peculiar property of the NO₂ group. In the experiment, the researchers used many compounds, for example, 3-Chloro-2-iodobenzoic acid (cas: 123278-03-5Recommanded Product: 123278-03-5).

3-Chloro-2-iodobenzoic acid (cas: 123278-03-5) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Recommanded Product: 123278-03-5

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis of eosinophil infiltration inhibitors with antihistaminic activity was written by Gyoten, Michiyo;Nagaya, Hideaki;Fukuda, Shigeru;Ashida, Yasuko;Kawano, Yasuhiko. And the article was included in Chemical & Pharmaceutical Bulletin in 2003.Computed Properties of C4H8ClI This article mentions the following:

A series of [1,2,4]triazolo[1,5-b]pyridazines and imidazo[1,2-b]pyridazines having cyclic amines was synthesized and evaluated for antihistaminic activity and inhibitory effect on eosinophil infiltration. When a piperidine or a piperazine containing a benzhydryl group and a suitable spacer was incorporated at the 6-position, the fused pyridazines were found to exhibit both antihistaminic activity and an inhibitory effect on eosinophil chemotaxis. Above all, one product showed potent antihistaminic activity, but little blockade of central H₁ receptors in contrast with its complete blockade of peripheral H₁ receptors as determined by an ex vivo binding assay. Furthermore, the same product inhibited eosinophil infiltration of the skin caused by a topical antigen challenge in sensitized guinea pigs, while an antihistamine terfenadine was not effective. After the pharmacokinetic study, this product was found to be rapidly hydrolyzed to 2-[6-[[3-[4-(diphenylmethoxy)-piperidino]propyl]amino]imidazo [1,2-b]pyridazin-2-yl]-2-methylpropionic acid dihydrate (TAK-427), which was also orally active. The later product having both antihistaminic and antiinflammatory activity, is currently undergoing clin. trials as a therapeutic agent for atopic dermatitis and allergic rhinitis. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Computed Properties of C4H8ClI).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Computed Properties of C4H8ClI

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com