Day: February 9, 2023

Discovery of Novel Spiroindoline Derivatives as Selective Tankyrase Inhibitors was written by Shirai, Fumiyuki;Tsumura, Takeshi;Yashiroda, Yoko;Yuki, Hitomi;Niwa, Hideaki;Sato, Shin;Chikada, Tsubasa;Koda, Yasuko;Washizuka, Kenichi;Yoshimoto, Nobuko;Abe, Masako;Onuki, Tetsuo;Mazaki, Yui;Hirama, Chizuko;Fukami, Takehiro;Watanabe, Hirofumi;Honma, Teruki;Umehara, Takashi;Shirouzu, Mikako;Okue, Masayuki;Kano, Yuko;Watanabe, Takashi;Kitamura, Kouichi;Shitara, Eiki;Muramatsu, Yukiko;Yoshida, Haruka;Mizutani, Anna;Seimiya, Hiroyuki;Yoshida, Minoru;Koyama, Hiroo. And the article was included in Journal of Medicinal Chemistry in 2019.Related Products of 58333-75-8 This article mentions the following:

The canonical WNT pathway plays an important role in cancer pathogenesis. Inhibition of poly(ADP-ribose) polymerase catalytic activity of the tankyrases (TNKS/TNKS2) has been reported to reduce the Wnt/β-catenin signal by preventing poly ADP-ribosylation dependent degradation of AXIN, a neg. regulator of Wnt/β-catenin signaling. With the goal of investigating the effects of tankyrase and Wnt pathway inhibition on tumor growth, we set out to find small mol. inhibitors of TNKS/TNKS2 with suitable drug-like properties. Starting from 1a(I), a high-throughput screening hit, the spiroindoline derivative 40c(II) (RK-287107) was discovered as a potent TNKS/TNKS2 inhibitor with >7,000-fold selectivity against the PARP1 enzyme, which inhibits WNT-responsive TCF reporter activity and proliferation of human colorectal cancer cell line COLO-320DM. II also demonstrated dose-dependent tumor growth inhibition in a mouse xenograft model. These observations suggest that II is a promising lead compound for the development of novel tankyrase inhibitors as anticancer agents. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Related Products of 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Related Products of 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of quinoxaline analogues was written by Chang, Meng-Yang;Lee, Tein-Wei;Hsu, Ru-Ting;Yen, Tzu-Lin. And the article was included in Synthesis in 2011.Name: 1-Tosylpiperidin-4-one This article mentions the following:

Substituted tricyclic or tetracyclic quinoxalines, tricyclic pyridoquinoxalines and bis-quinoxalines were synthesized in high yields starting from cyclic ketones by the α-bromination of cyclic ketones with N-bromosuccinimide (NBS) followed by condensation of the resulting α-bromo ketones with 1,2-diaminobenzene, 3,4-diaminopyridine, or 3,3′-diaminobenzidine. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Name: 1-Tosylpiperidin-4-one).

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. 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.Name: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

New xanthine derivatives with potent and long lasting anti-bronchoconstrictive activity was written by Regnier, Gilbert L.;Guillonneau, Claude G.;Duhault, Jacques L.;Tisserand, Francoise P.;Saint-Romas, Guy;Holstorp, Sophie M.. And the article was included in European Journal of Medicinal Chemistry in 1987.Synthetic Route of C7H13NO2 This article mentions the following:

Twenty-nine new derivatives of 8-aminoalkyl-substituted xanthine [e.g. I, R¹ = H, Me, Et; R² = Me, iso-Pr, Ph, etc.; R³ = H, Me, 2,3-dihydroxypropyl, etc.; R⁴ = H or F; and X = CH(OH)CH₂, (CH₂)_n; n = 1-3] were synthesized. All I demonstrated a potent anti-bronochoconstrictive effect in the guinea pig and some had a very long duration of action (> 48h). II was selected for clin. trials in asthmatic patients because of its long duration of action, its lack of central nervous system-stimulating effects and its inhibiting action on mast cell degranulation and phosphodiesterse activity. Structure-activity relationships are discussed. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Synthetic Route of C7H13NO2).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Synthetic Route of C7H13NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and Antimalarial-Activity Evaluation of Tetraoxane-Triazine Hybrids and Spiro[piperidine-4,3′-tetraoxanes] was written by Kumar, Nitin;Khan, Shabana I.;Rawat, Diwan S.. And the article was included in Helvetica Chimica Acta in 2012.Recommanded Product: 1-Tosylpiperidin-4-one This article mentions the following:

A series of tetraoxane-triazine hybrids and spiro[piperidine-4,3′-tetraoxanes] have been synthesized, and all the compounds were screened for in vitro antimalarial activity against chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Most of the spiro[piperidine-4,3′-tetraoxanes] exhibited moderate to good antimalarial activities, and two compounds I and II have shown good antimalarial activity with IC₅₀ values in the range of 0.30 to 0.70 μM against both the strains with a high selectivity index and no cytotoxicity towards mammalian kidney cell line. 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. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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

Metallaphotoredox-enabled deoxygenative arylation of alcohols was written by Dong, Zhe;MacMillan, David W. C.. And the article was included in Nature (London, United Kingdom) in 2021.Computed Properties of C11H21NO3 This article mentions the following:

Metal-catalyzed cross-couplings are a mainstay of organic synthesis and are widely used for the formation of C-C bonds, particularly in the production of unsaturated scaffolds1. However, alkyl cross-couplings using native sp3-hybridized functional groups such as alcs. remain relatively underdeveloped2. In particular, a robust and general method for the direct deoxygenative coupling of alcs. would have major implications for the field of organic synthesis. A general method for the direct deoxygenative cross-coupling of free alcs. must overcome several challenges, most notably the in situ cleavage of strong C-O bonds3, but would allow access to the vast collection of com. available, structurally diverse alcs. as coupling partners4. Authors report herein a metallaphotoredox-based cross-coupling platform in which free alcs. are activated in situ by N-heterocyclic carbene salts for carbon-carbon bond formation with aryl halide coupling partners. This method is mild, robust, selective and most importantly, capable of accommodating a wide range of primary, secondary and tertiary alcs. as well as pharmaceutically relevant aryl and heteroaryl bromides and chlorides. The power of the transformation has been demonstrated in a number of complex settings, including the late-stage functionalization of Taxol and a modular synthesis of Januvia, an antidiabetic medication. This technol. represents a general strategy for the merger of in situ alc. activation with transition metal catalysis. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Computed Properties of C11H21NO3).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Computed Properties of C11H21NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A convenient synthesis of functionalized 8- and 9-aza-1-oxaspiro[5.5]undecanes was written by Apostolopoulos, Costas D.;Haroutounian, Serkos A.. And the article was included in Journal of Heterocyclic Chemistry in 1995.Application of 95798-22-4 This article mentions the following:

2-Hydroxy-8-(or 9-)aza-1-oxaspiro[5.5]undec-3-en-5-ones derived from their corresponding 2-furfuryl alcs. were used as key intermediates for the convenient synthesis of several novel 8- and 9-aza-1-oxaspiro[5.5]undecane derivatives In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4Application of 95798-22-4).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) 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. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Application of 95798-22-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of aryl (alkyl) ketones of the piperidine series was written by Kuroyan, R. A.;Markosyan, A. I.;Snkhchyan, G. M.;Vartanyan, S. A.. And the article was included in Armyanskii Khimicheskii Zhurnal in 1983.COA of Formula: C13H16N2 This article mentions the following:

Alkyl (aryl) piperidinyl ketones I [R = PhCH₂, R¹ = H, R² = C_1-5 n-alkyl, (un)substituted Ph, PhCH₂; R = R¹ = Me, R² = (un)substituted Ph, PhCH₂] were prepared from the corresponding piperidinecarboxaldehyde by oximation, dehydration to the nitrile and Grignard reaction with R²X (X = undefined halo). In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4COA of Formula: C13H16N2).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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.COA of Formula: C13H16N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Rearrangement of Hydroxylated Pinene Derivatives to Fenchone-Type Frameworks: Computational Evidence for Dynamically-Controlled Selectivity was written by Blumel, Marcus;Nagasawa, Shota;Blackford, Katherine;Hare, Stephanie R.;Tantillo, Dean J.;Sarpong, Richmond. And the article was included in Journal of the American Chemical Society in 2018.Related Products of 33439-27-9 This article mentions the following:

An acid-catalyzed Prins/semipinacol rearrangement cascade reaction of hydroxylated pinene derivatives that leads to tricyclic fenchone-type scaffolds in very high yields and diastereoselectivity has been developed. Quantum chem. anal. of the selectivity-determining step provides support for the existence of an extremely flat potential energy surface around the transition state structure. This transition state structure appears to be ambimodal, i.e., the fenchone-type tricyclic scaffolds are formed in preference to the competing formation of a bornyl (camphor-type) skeleton under dynamic control via a post-transition state bifurcation (PTSB). 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. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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.Related Products of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthetic bacteriochlorins with integral spiro-piperidine motifs was written by Reddy, Kanumuri Ramesh;Lubian, Elisa;Pavan, M. Phani;Kim, Han-Je;Yang, Eunkyung;Holten, Dewey;Lindsey, Jonathan S.. And the article was included in New Journal of Chemistry in 2013.Electric Literature of C12H15NO3S This article mentions the following:

A new mol. design incorporates a spiro-piperidine unit in each pyrroline ring of synthetic bacteriochlorins, thereby (1) replacing the previous geminal di-Me group with a functionally equivalent motif to suppress adventitious dehydrogenation, (2) enabling tailoring of the bacteriochlorin by nitrogen derivatization, and (3) leaving the β-pyrrolic positions available for introduction of auxochromes to tune the spectral properties. Conversion of an N-protected 4-piperidone to the N-protected α,β-unsaturated ketone, Michael reaction with 4-(ethoxycarbonyl)-3-ethyl-2-(2-nitroethyl)pyrrole (I), and subsequent reductive cyclization provided the spiro-piperidine-1-methyldihydrodipyrrin (II; R = Ts, Boc; R¹ = H, Me). Treatment with SeO₂ followed by tri-Me orthoformate under acid catalysis converted the 1-Me group to a 1-(1,1-dimethoxymethyl) motif. Self-condensation of the resulting spiro-piperidine-dihydrodipyrrin-acetal afforded the 5-methoxy- or 5-unsubstituted bacteriochlorins III (R = Ts, Boc; R² = H, OMe), each bearing two spiro-piperidine units. The spiro-piperidine units were derivatized at the nitrogens by methylation, sulfonylation, acylation, or quaternization; the latter with Me iodide afforded two dicationic, hydrophilic bacteriochlorins. Altogether, eight spiro-piperidine-bacteriochlorins were prepared Spectroscopic characterization was carried out in DMF (and in water for the quaternized, 5-methoxybacteriochlorin). Compared to the 5-unsubstituted analog, the quaternized, 5-methoxybacteriochlorin has in DMF a shorter wavelength of the intense near-IR absorption band (733 vs. 752 nm) and fluorescence band (739 vs. 760 nm), modestly greater fluorescence yield (0.15 vs. 0.08) and modestly longer lifetime of the lowest singlet excited state (4.7 vs. 3.3 ns). In general, the spiro-piperidinyl moiety does not significantly alter the rate constants or yields of the decay pathways (fluorescence, intersystem crossing, internal conversion) of the lowest singlet excited state of the bacteriochlorin. Taken together, the results describe a new mol. design for tailoring the polarity of near-IR absorbers. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Electric Literature of C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of 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.Electric Literature of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis was written by Reed, Nicholas L.;Herman, Madeline I.;Miltchev, Vladimir P.;Yoon, Tehshik P.. And the article was included in Organic Letters in 2018.Computed Properties of C12H15NO3S This article mentions the following:

A photocatalytic method for the oxyamination of alkenes using simple nucleophilic nitrogen atom sources in place of prefunctionalized electrophilic nitrogen atom donors is reported. Copper(II) is an inexpensive, practical, and uniquely effective terminal oxidant for this process. In contrast to oxygen, peroxides, and similar oxidants commonly utilized in non-photochem. oxidative methods, the use of copper(II) as a terminal oxidant in photoredox reactions avoids the formation of reactive heteroatom-centered radical intermediates that can be incompatible with electron-rich functional groups. As a demonstration of the generality of this concept, it has been shown that diamination and deoxygenation reactions can also be accomplished using similar photooxidative conditions. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Computed Properties of C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.Computed Properties of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem