Tag: 200-300

Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents was written by Lou, Terry Shing-Bong;Bagley, Scott W.;Willis, Michael C.. And the article was included in Angewandte Chemie, International Edition in 2019.HPLC of Formula: 33439-27-9 This article mentions the following:

A series of low-mol.-weight, compact, and multifunctional cyclic alkenylsulfonyl fluorides were efficiently prepared from the corresponding alkenyl triflates. Palladium-catalyzed sulfur dioxide insertion using the surrogate reagent DABSO effects sulfinate formation, before trapping with an F electrophile delivers the sulfonyl fluorides. A broad range of functional groups are tolerated, and a correspondingly large collection of derivatization reactions are possible on the products, including substitution at sulfur, conjugate addition, and N-functionalization. Together, these attributes suggest that this method could find new applications in chem. biol. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9HPLC of Formula: 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.HPLC of Formula: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of Bridged Azacycles and Propellanes via Nitrene/Alkyne Cascades was written by Wang, Qinxuan;May, Jeremy A.. And the article was included in Organic Letters in 2020.Safety of 1-Tosylpiperidin-4-one This article mentions the following:

A nitrene/alkyne cascade reaction terminating in C-H bond insertion to form functionalized bridged azacycles from carbonazidates is presented. Due to an initial Huisgen cyclization, all carbonazidates reacted with the alkyne in an exo mode in contrast to the use of sulfamate esters, which react predominately in an endo mode. Substrates with different ring sizes as well as different aryl and heteroaryl groups were also explored. Variation of the nitrene tether showed that 7-membered rings were the maximum ring size to be formed by nitrene attack on the alkyne. Examples incorporating stereocenters on the carbonazidate’s tether induced diasteroselectivity in the formation of the bridged ring and two new stereocenters. Addnl., propellanes containing aminals, hemiaminals, and thioaminals formed from the bridged azacycles in the same reaction via an acid-promoted rearrangement. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Safety of 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Safety of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

1-(1,3-Benzodioxol-5-ylmethyl)-3-[4-(1H-imidazol-1-yl)phenoxy]-piperidine analogs as potent and selective inhibitors of nitric oxide formation was written by Wei, Robert G.;Adler, Marc;Davey, David;Ho, Elena;Mohan, Raju;Polokoff, Mark;Tseng, Jih-Lie;Whitlow, Marc;Xu, Wei;Yuan, Shendong;Phillips, Gary. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Formula: C12H18ClNO This article mentions the following:

A new series of 1-(1,3-benzodioxol-5-ylmethyl)-3-[4-(1H-Imidazol-1-yl)phenoxy]-piperidine analogs were designed and identified as potent and selective inhibitors of NO formation based both on the crystal structure of a murine iNOS Δ114 monomer domain/ inhibitor complex and inhibition of the NO formation in human A172 cell assays. Compound 12S showed high potency and high iNOS selectivity vs. nNOS and eNOS. In the experiment, the researchers used many compounds, for example, 1-Benzyl-3-piperidinol hydrochloride (cas: 105973-51-1Formula: C12H18ClNO).

1-Benzyl-3-piperidinol hydrochloride (cas: 105973-51-1) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Formula: C12H18ClNO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell was written by Green, Robert A.;Jolley, Katherine E.;Al-Hadedi, Azzam A. M.;Pletcher, Derek;Harrowven, David C.;De Frutos, Oscar;Mateos, Carlos;Klauber, David J.;Rincon, Juan A.;Brown, Richard C. D.. And the article was included in Organic Letters in 2017.Related Products of 33439-27-9 This article mentions the following:

Electrochem. deprotection of p-methoxybenzyl (PMB) ethers was performed in an undivided electrochem. flow reactor in MeOH solution, leading to the unmasked alc. and p-methoxybenzaldehyde di-Me acetal as a byproduct. The electrochem. method removes the need for chem. oxidants, and added electrolyte (BF₄NEt₄) can be recovered and reused. The method was applied to 17 substrates with high conversions in a single pass, yields up to 92%, and up to 7.5 g h^-1 productivity. The PMB protecting group was also selectively removed in the presence of some other common alc. protecting groups. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Related Products of 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Related Products of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Molecular determinants for recognition of RU 24696 analogs at central 5-hydroxytryptamine recognition sites: use of a bilinear function and substituent volumes to describe steric fit was written by Taylor, Ethan Will;Nikam, Sham S.;Lambert, Georgina;Martin, Arnold R.;Nelson, David L.. And the article was included in Molecular Pharmacology in 1988.Reference of 33439-27-9 This article mentions the following:

The putative serotonin (5-HT) agonist RU 24969 (I) has been extensively used in the study and classification of 5-HT receptors. To study mol. determinants for recognition of 1,2,3,6-tetrahydropyridin-4-ylindoles (THP) at central 5-HT recognition sites, about 25 addnl. THP derivatives were synthesized, incorporating, among others, 16 different indole-5-substituents and 3 different pyridine-N substituents in various combinations. Two saturated derivatives (piperidin-4-ylindoles) and 2 2-Me analogs were also included. Binding affinities at 5-HT_1A, 5-HT₂, and total 5-HT₁ sites were obtained and the data were incorporated in quant. structure-activity relations (QSARs) using a combined linear free energy/mol. modeling approach. The QSAR analyses suggest distinct differences in the structural features that determine optimal potency at 5-HT_1A sites vs. those directing optima potency for 5-HT₂ sites. The parameter of the indole-5 substituent that almost exclusively determines potency for 5-HT_1A sites is volume, the optimal size being about 24 cubic angstroms (calculated by fitting the activity vs. volume data to a bilinear function). This is approx. the size of a carboxamide group. In contrast, at the 5-HT₂ site both volume and hydrophobicity play a major but opposing roles for the 5-substituent. A balance between the smallest possible volume and the greatest possible hydrophobicity is required for maximal 5-HT₂ potency. Benzyl groups on the indole-1 or pyridyl-1 positions also favor potency at the 5-HT₂ site (probably largely due to increased hydrophobic binding) while decreasing potency at the 5-HT_1A site. A minor electronic contribution to the QSARs involving the charge on the indole 5-carbon is of opposite sign for 5-HT_1A vs. 5-HT₂ sites and thus may also be useful for selective drug design. The data are consistent with the possibility that the indole and pyridyl rings are in a coplanar configuration when binding at both 5-HT_1A and 5-HT₂ sites, because the indole-2-Me substituent, which provides a large energy barrier to the coplanar configuration, greatly reduces the potency of THP at both binding sites. Similarities in analog selectivity patterns suggest that the indole portion of these compounds binds similarly to that of other indole derivatives such as tryptamines; thus, it is possible that optimally selective substituents predicted by these QSARs may be extrapolated to tryptamines and other indoles. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Reference of 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Reference of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties was written by Rasson, Corentin;Stouse, Adrien;Boreux, Arnaud;Cirriez, Virginie;Riant, Olivier. And the article was included in Chemistry – A European Journal in 2018.Recommanded Product: 1-Tosylpiperidin-4-one This article mentions the following:

Herein, we report the copper-catalyzed domino borylation/aldolisation of Me 2-fluoroacrylate with carbonyl compounds followed by an elimination to give Morita-Baylis-Hillman (MBH) analogs. The optimal conditions described were shown to be compatible with a wide range of aldehydes and ketones. Unprecedented MBH adducts derived from ketones were efficiently synthesized. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Recommanded Product: 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Recommanded Product: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening/Alkylation Sequence was written by Ito, Tomohiro;Tsutsumi, Masaki;Yamada, Ken-ichi;Takikawa, Hiroshi;Yamaoka, Yousuke;Takasu, Kiyosei. And the article was included in Angewandte Chemie, International Edition in 2019.Synthetic Route of C12H15NO3S This article mentions the following:

Development of a novel synthetic method for medium-sized trans-cycloalkenes (TCAs), e.g., I is described. Functionalized TCAs e.g., I are readily prepared from simple cycloalkanone such as tert-butyl(cyclohept-1-en-1-yloxy)dimethylsilane, in a few steps, namely, enol silyl ether formation, [2+2] cycloaddition, and domino 4π electrocyclic ring opening/alkylation (conjugate addition). The first example of central-to-planar chirality transfer from enantiomerically enriched cyclobutenes, e.g., II to TCAs e.g., I is also described. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Synthetic Route of C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Catalytic Asymmetric α-Alkylation of Ketones and Aldehydes with N-Benzylic Sulfonamides through Carbon-Nitrogen Bond Cleavage was written by Weng, Zhen-Tao;Li, Yuan;Tian, Shi-Kai. And the article was included in Journal of Organic Chemistry in 2011.Formula: C12H15NO3S This article mentions the following:

A range of ketones and aldehydes smoothly undergoes asym. S_N1 α-alkylation with N-benzylic sulfonamides in the presence of 10 mol % of a chiral imidazolidinone and trifluoroacetic acid to give the corresponding products in good to excellent yields and with good enantioselectivity. This chem. has been successfully extended to the asym. desymmetrization of 4-substituted cyclohexanones, which exhibits greater than 99:1 diastereoselectivity and good enantioselectivity. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Formula: C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Formula: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Methyl Radical Initiated Kharasch and Related Reactions was written by Tappin, Nicholas D. C.;Renaud, Philippe. And the article was included in Advanced Synthesis & Catalysis in 2021.Synthetic Route of C12H15NO3S This article mentions the following:

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive Me radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N₂) or volatile (acetone and Me halide) thereby facilitating greatly product purification by either flash column chromatog. or distillation In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 min under normal atm.) and a low excess of the radical precursor reagent (2 equiv) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-Bu peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous byproducts (CO₂). In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Synthetic Route of C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Structure-Based Optimization of Thiophene[3,2-d]pyrimidine Derivatives as Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors with Improved Potency against Resistance-Associated Variants was written by Kang, Dongwei;Fang, Zengjun;Huang, Boshi;Lu, Xueyi;Zhang, Heng;Xu, Haoran;Huo, Zhipeng;Zhou, Zhongxia;Yu, Zhao;Meng, Qing;Wu, Gaochan;Ding, Xiao;Tian, Ye;Daelemans, Dirk;De Clercq, Erik;Pannecouque, Christophe;Zhan, Peng;Liu, Xinyong. And the article was included in Journal of Medicinal Chemistry in 2017.Name: tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate This article mentions the following:

This work follows on from our initial discovery of a series of piperidine-substituted thiophene[3,2-d]pyrimidine HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTI) (J. Med. Chem. 2016, 59, 7991-8007). In the present study, we designed, synthesized, and biol. tested several series of new derivatives in order to investigate previously unexplored chem. space. Some of the synthesized compounds displayed single-digit nanomolar anti-HIV potencies against wild-type (WT) virus and a panel of NNRTI-resistant mutant viruses in MT-4 cells. I was exceptionally potent against the whole viral panel, affording 3-4-fold enhancement of in vitro antiviral potency against WT, L100I, K103N, Y181C, Y188L, E138K, and K103N+Y181C and 10-fold enhancement against F227L+V106A relative to the reference drug etravirine (ETV) in the same cellular assay. The structure-activity relationships, pharmacokinetics, acute toxicity, and cardiotoxicity were also examined Overall, the results indicate that I is a promising new drug candidate for treatment of HIV-1 infection. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate (cas: 934536-10-4Name: tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate).

tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate (cas: 934536-10-4) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Name: tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem