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Статті в журналах з теми "Endo selective"

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Автор: Grafiati

Опубліковано: 10 грудня 2022

Оновлено: 28 січня 2023

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1

Fujiwara, Kenshu, Hirohumi Mishima, Arika Amano, Tetsuo Tokiwano, and Akio Murai. "La(OTf)3-catalyzed 7-endo and 8-endo selective cyclizations of hydroxy epoxides." Tetrahedron Letters 39, no. 5-6 (January 1998): 393–96. http://dx.doi.org/10.1016/s0040-4039(97)10557-3.

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2

Parasram, Marvin, Viktor O. Iaroshenko, and Vladimir Gevorgyan. "Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction." Journal of the American Chemical Society 136, no. 52 (December 17, 2014): 17926–29. http://dx.doi.org/10.1021/ja5104525.

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3

Bridge, Benjamin J., Paul D. Boyle, and Johanna M. Blacquiere. "endo-Selective Iron Catalysts for Intramolecular Alkyne Hydrofunctionalization." Organometallics 39, no. 14 (July 6, 2020): 2570–74. http://dx.doi.org/10.1021/acs.organomet.0c00307.

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4

BECKMANN, M., T. MEYER, F. SCHULZ, and E. WINTERFELDT. "ChemInform Abstract: Face-Selective and endo-Selective Cycloadditions with Enantiomerically Pure Cyclopentadienes." ChemInform 26, no. 20 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199520101.

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5

Lording, William J., Thomas Fallon, Michael S. Sherburn, and Michael N. Paddon-Row. "The simplest Diels–Alder reactions are not endo-selective." Chemical Science 11, no. 43 (2020): 11915–26. http://dx.doi.org/10.1039/d0sc04553e.

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6

Tanase, Constantin I., Constantin Draghici, Catalina Negut, and Lucia Pintilie. "New Constrained Amines in a Bicyclo[2.2.1]Heptane Skeleton." Revista de Chimie 69, no. 9 (October 15, 2018): 2448–53. http://dx.doi.org/10.37358/rc.18.9.6551.

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Анотація:

In this paper we present an efficient procedure for obtaining ether-protected bicyclo[2.2.1]heptane amines in six steps, from an optically active keto-alcohol norbornane compound, for building the heterocyclic bases of pyrimidine and purine constrained nucleosides. Trityl as protecting group makes it possible to isolate 5-endo-compounds in pure form by selective crystallization, and to isolate the intermediates in the next 3 steps of the reaction by crystallization. With TBDMS, all compounds were obtained as oil. The direct selective reduction of the keto-alcohol norbornane compound gave the pure 5-endo-diol 4d in high yield, which was then selectively protected at the primary hydroxyl with a trityl group; the next steps are similar for obtaining the trityl-protected bicyclo[2.2.1]heptane amine. The azide intermediates are valuable intermediates for click chemistry.

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7

Christov, Plamen P., Surajit Banerjee, Michael P. Stone та Carmelo J. Rizzo. "Selective Incision of theα-N5-Methyl-Formamidopyrimidine Anomer byEscherichia coliEndonuclease IV". Journal of Nucleic Acids 2010 (2010): 1–10. http://dx.doi.org/10.4061/2010/850234.

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Formamidopyrimidines (Fapy) lesions result from ring opening of the imidazole portion of purines. Fapy lesions can isomerize from the naturalβ-anomeric stereochemistry to theα-configuration. We have unambiguously demonstrated that theα-methyl-Fapy-dG (MeFapy-dG) lesion is a substrate forEscherichia coliEndonuclease IV (Endo IV). Treatment of a MeFapy-dG-containing 24 mer duplex with Endo IV resulted in 36–40% incision. The catalytic efficiency of the incision was comparable to that ofα-dG in the same duplex sequence. Theα- andβ-MeFapy-dG anomers equilibrate to ~21 : 79 ratio over ~3 days. Related studies with a duplex containing theα-Fapy-dG lesion derived from aflatoxin B1epoxide (α-AFB-Fapy-dG) showed only low levels of incision. It is hypothesized that the steric bulk of the aflatoxin moiety interferes with the binding of the substrate to Endo IV and the incision chemistry.

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8

Tesz, Gregory J., Myriam Aouadi, Matthieu Prot, Sarah M. Nicoloro, Emilie Boutet, Shinya U. Amano, Anca Goller, et al. "Glucan particles for selective delivery of siRNA to phagocytic cells in mice." Biochemical Journal 436, no. 2 (May 13, 2011): 351–62. http://dx.doi.org/10.1042/bj20110352.

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Phagocytic macrophages and dendritic cells are desirable targets for potential RNAi (RNA interference) therapeutics because they often mediate pathogenic inflammation and autoimmune responses. We recently engineered a complex 5 component glucan-based encapsulation system for siRNA (small interfering RNA) delivery to phagocytes. In experiments designed to simplify this original formulation, we discovered that the amphipathic peptide Endo-Porter forms stable nanocomplexes with siRNA that can mediate potent gene silencing in multiple cell types. In order to restrict such gene silencing to phagocytes, a method was developed to entrap siRNA–Endo-Porter complexes in glucan shells of 2–4 μm diameter in the absence of other components. The resulting glucan particles containing fluorescently labelled siRNA were readily internalized by macrophages, but not other cell types, and released the labelled siRNA into the macrophage cytoplasm. Intraperitoneal administration of such glucan particles containing siRNA–Endo-Porter complexes to mice caused gene silencing specifically in macrophages that internalized the particles. These results from the present study indicate that specific targeting to phagocytes is mediated by the glucan, whereas Endo-Porter peptide serves both to anchor siRNA within glucan particles and to catalyse escape of siRNA from phagosomes. Thus we have developed a simplified siRNA delivery system that effectively and specifically targets phagocytes in culture or in intact mice.

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9

Rigby, James H., Robert C. Hughes, and Mary Jane Heeg. "Endo-Selective Cyclization Pathways in the Intramolecular Heck Reaction." Journal of the American Chemical Society 117, no. 29 (July 1995): 7834–35. http://dx.doi.org/10.1021/ja00134a040.

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10

FUJIWARA, K., H. MISHIMA, A. AMANO, T. TOKIWANO, and A. MURAI. "ChemInform Abstract: La(OTf)3-Catalyzed 7-endo and 8-endo Selective Cyclizations of Hydroxy Epoxides." ChemInform 29, no. 14 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199814142.

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11

Sun, Jun, Ying R. Huang, William R. Harrington, Shubin Sheng, John A. Katzenellenbogen та Benita S. Katzenellenbogen. "Antagonists Selective for Estrogen Receptor α". Endocrinology 143, № 3 (березень 2002): 941–47. http://dx.doi.org/10.1210/endo.143.3.8704.

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12

Hennebold, Jon D., Mamoru Tanaka, Juichiro Saito, Berkely R. Hanson, and Eli Y. Adashi. "Ovary-Selective Genes I: The Generation and Characterization of an Ovary-Selective Complementary Deoxyribonucleic Acid Library*." Endocrinology 141, no. 8 (August 1, 2000): 2725–34. http://dx.doi.org/10.1210/endo.141.8.7627.

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13

Giddens, John P., Joseph V. Lomino, David J. DiLillo, Jeffrey V. Ravetch, and Lai-Xi Wang. "Site-selective chemoenzymatic glycoengineering of Fab and Fc glycans of a therapeutic antibody." Proceedings of the National Academy of Sciences 115, no. 47 (November 5, 2018): 12023–27. http://dx.doi.org/10.1073/pnas.1812833115.

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Анотація:

The N-glycans attached to the Fab and Fc domains play distinct roles in modulating the functions of antibodies. However, posttranslational site-selective modifications of glycans in antibodies and other multiply glycosylated proteins remain a challenging task. Here, we report a chemoenzymatic method that permits independent manipulation of the Fab and Fc N-glycans, using cetuximab as a model therapeutic monoclonal antibody. Taking advantage of the substrate specificity of three endoglycosidases (Endo-S, Endo-S2, and Endo-F3) and their glycosynthase mutants, together with an unexpected substrate site-selectivity of a bacterial α1,6-fucosidase from Lactobacillus casei (AlfC), we were able to synthesize an optimal homogeneous glycoform of cetuximab in which the heterogeneous and immunogenic Fab N-glycans were replaced with a single sialylated N-glycan, and the core-fucosylated Fc N-glycans were remodeled with a nonfucosylated and fully galactosylated N-glycan. The glycoengineered cetuximab demonstrated increased affinity for the FcγIIIa receptor and significantly enhanced antibody-dependent cell-mediated cytotoxicity (ADCC) activity.

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14

Hasebe, N., Y. T. Shen, K. Kiuchi, L. Hittinger, S. P. Bishop, and S. F. Vatner. "Enhanced postischemic dysfunction selective to subendocardium in conscious dogs with LV hypertrophy." American Journal of Physiology-Heart and Circulatory Physiology 266, no. 2 (February 1, 1994): H702—H713. http://dx.doi.org/10.1152/ajpheart.1994.266.2.h702.

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The effects of a 15-min coronary arterial occlusion (CAO) and reperfusion (CAR) for 24 h were compared in 11 normal dogs and in 13 conscious dogs with left ventricular (LV) hypertrophy (H) induced by ascending aortic banding, which increased the LV weight-to-body weight ratio by 69%. The dogs were studied 2–4 wk after recovery from instrumentation for measurement of global LV dynamics and regional wall motion. During CAO, heart rate and LV end-diastolic pressure increased similarly in both groups; however, LV systolic pressure decreased (-38 +/- 6 mmHg; P < 0.01) only in LVH. At 1 h of CAR, all measurements of systemic hemodynamics and global LV function returned to baseline levels in normal dogs; however, sustained depression (P < 0.01) in LV systolic pressure (-18 +/- 4 mmHg) and mean velocity of circumferential fiber shortening corrected for heart rate (-0.17 +/- 0.06) were observed in LVH. The recovery in regional myocardial dysfunction was significantly prolonged in the subendocardium (Endo) of LVH, e.g., at 1 h of CAR, Endo wall thickening was depressed more in dogs with LVH compared with normal dogs (-69 +/- 3% vs. -53 +/- 5%; P < 0.01), but not in the subepicardium (Epi). Coronary flow reserve, assessed by intravenous adenosine, was depressed in Endo of LVH compared with normal dogs, but not altered further by CAR. In conclusion, myocardial stunning after a brief period of CAO in dogs with LVH was not enhanced in Epi but was modestly increased in Endo. This regional dysfunction was, however, sufficiently powerful to induce modest impairment of global LV function.

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15

Jaślan, Dawid, Julia Böck, Einar Krogsaeter, and Christian Grimm. "Evolutionary Aspects of TRPMLs and TPCs." International Journal of Molecular Sciences 21, no. 11 (June 11, 2020): 4181. http://dx.doi.org/10.3390/ijms21114181.

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Transient receptor potential (TRP) or transient receptor potential channels are a highly diverse family of mostly non-selective cation channels. In the mammalian genome, 28 members can be identified, most of them being expressed predominantly in the plasma membrane with the exception of the mucolipins or TRPMLs which are expressed in the endo-lysosomal system. In mammalian organisms, TRPMLs have been associated with a number of critical endo-lysosomal functions such as autophagy, endo-lysosomal fusion/fission and trafficking, lysosomal exocytosis, pH regulation, or lysosomal motility and positioning. The related non-selective two-pore cation channels (TPCs), likewise expressed in endosomes and lysosomes, have also been found to be associated with endo-lysosomal trafficking, autophagy, pH regulation, or lysosomal exocytosis, raising the question why these two channel families have evolved independently. We followed TRP/TRPML channels and TPCs through evolution and describe here in which species TRP/TRPMLs and/or TPCs are found, which functions they have in different species, and how this compares to the functions of mammalian orthologs.

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16

Mayans, Júlia, Mercé Font-Bardia, and Albert Escuer. "Lithium cations in a self-assembled electrostatic nanocapsule." Dalton Transactions 48, no. 43 (2019): 16158–61. http://dx.doi.org/10.1039/c9dt03600h.

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A self-assembled {Ni₁₂Li₂} nanometric capsule with endo- and exo-guests linked to selective hydrophilic/hydrophobic binding sites of Ni^II₆ rings was achieved by using (Bu₄N)N₃ instead of sodium azide to selectively introduce the Li⁺ cations.

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17

Karmakar, Swastik, Prasanta Das, and Sandip Kundu. "Silver-catalyzed tandem 5- and 6-endo-cyclizations via concomitant yne-ol-imine activation: selective entry to 2-aryldihydrofuroquinolines." New Journal of Chemistry 45, no. 35 (2021): 16112–18. http://dx.doi.org/10.1039/d1nj02643g.

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Ag(i)-catalyzed domino imination-intramolecular bi-heterocyclization-aromatization cascade has been developed to construct 2-aryldihydrofuroquinolines from aldehyde and unprotected 4-(2-aminophenyl)but-3-yn-1-ol via tandem 5-endo-dig and 6-endo-trig cyclization.

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18

Huang, Guobao, Arto Valkonen, Kari Rissanen, and Wei Jiang. "endo-Functionalized molecular tubes: selective encapsulation of neutral molecules in non-polar media." Chemical Communications 52, no. 58 (2016): 9078–81. http://dx.doi.org/10.1039/c6cc00349d.

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19

Foster, Robert W., Laure Benhamou, Michael J. Porter, Dejan-Kresimir Bucar, Helen C. Hailes, Christopher J. Tame, and Tom D. Sheppard. "ChemInform Abstract: Irreversible endo-Selective Diels-Alder Reactions of Substituted Alkoxyfurans: A General Synthesis of endo-Cantharimides." ChemInform 46, no. 35 (August 13, 2015): no. http://dx.doi.org/10.1002/chin.201535026.

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20

Ishibashi, Hiroyuki, Tsuyoshi Taniguchi, and Hisaaki Zaimoku. "8-Endo-Selective Aryl Radical Cyclization Leading to 3-Benzazocines." HETEROCYCLES 77, no. 1 (2009): 575. http://dx.doi.org/10.3987/com-08-s(f)21.

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21

Morten, Christopher J., Jeffery A. Byers, Aaron R. Van Dyke, Ivan Vilotijevic, and Timothy F. Jamison. "The development of endo-selective epoxide-opening cascades in water." Chemical Society Reviews 38, no. 11 (2009): 3175. http://dx.doi.org/10.1039/b816697h.

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22

Valkonen, Arto, Wei Jiang, and Kari Rissanen. "Selective encapsulation of neutral molecules by endo-functionalized molecular tubes." Acta Crystallographica Section A Foundations and Advances 72, a1 (August 28, 2016): s386. http://dx.doi.org/10.1107/s2053273316094341.

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23

Singer, Robert D., Ivan Hemeon, Carolyn DeAmicis, Hilary Jenkins, and Peter Scammells. "Endo Selective Diels-Alder Reactions of Furan in Ionic Liquids." Synlett 2002, no. 11 (2002): 1815–18. http://dx.doi.org/10.1055/s-2002-34868.

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24

Kopcho, Joseph J., and James C. Schaeffer. "Selective O-demethylation of 7.alpha.-(aminomethyl)6,14-endo-ethenotetrahydrothebaine." Journal of Organic Chemistry 51, no. 9 (May 1986): 1620–22. http://dx.doi.org/10.1021/jo00359a053.

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25

Spisak, Sarah N., Alexander V. Zabula, Alexander S. Filatov, Andrey Yu Rogachev, and Marina A. Petrukhina. "Selective Endo and Exo Binding of Alkali Metals to Corannulene." Angewandte Chemie 123, no. 35 (July 11, 2011): 8240–44. http://dx.doi.org/10.1002/ange.201103028.

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26

Spisak, Sarah N., Alexander V. Zabula, Alexander S. Filatov, Andrey Yu Rogachev, and Marina A. Petrukhina. "Selective Endo and Exo Binding of Alkali Metals to Corannulene." Angewandte Chemie International Edition 50, no. 35 (July 11, 2011): 8090–94. http://dx.doi.org/10.1002/anie.201103028.

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27

Parasram, Marvin, Viktor O. Iaroshenko, and Vladimir Gevorgyan. "ChemInform Abstract: endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction." ChemInform 46, no. 25 (June 2015): no. http://dx.doi.org/10.1002/chin.201525224.

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28

Maeda, Hajime, Hiroki Takenaka, and Kazuhiko Mizuno. "Intermolecular hydrogen bonding controlled stereoselective photocycloaddition of vinyl ethers to 1-cyanonaphthalenes." Photochemical & Photobiological Sciences 15, no. 11 (2016): 1385–92. http://dx.doi.org/10.1039/c6pp00281a.

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29

Yamashita, Yasuhiro, Liang Cheng Nam, Mark J. Dutton, Susumu Yoshimoto та Shū Kobayashi. "Catalytic asymmetric endo-selective [3+2] cycloaddition reactions of Schiff bases of α-aminophosphonates with olefins using chiral metal amides". Chemical Communications 51, № 96 (2015): 17064–67. http://dx.doi.org/10.1039/c5cc07066j.

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30

Li, Na, Xianrui Liang, and Weike Su. "New insights into the asymmetric Diels–Alder reaction: the endo- and S-selective retro-Diels–Alder reaction." RSC Advances 5, no. 128 (2015): 106234–38. http://dx.doi.org/10.1039/c5ra17788j.

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31

Depken, Christian, Felix Krätzschmar, and Alexander Breder. "Iodine(iii)-mediated oxidative intramolecular arene–alkene coupling exemplified in the synthesis of phenanthrenes." Organic Chemistry Frontiers 3, no. 3 (2016): 314–18. http://dx.doi.org/10.1039/c5qo00361j.

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32

Meloncelli, Peter J., Tracey M. Gloster, Victoria A. Money, Chris A. Tarling, Gideon J. Davies, Stephen G. Withers та Robert V. Stick. "D-Glucosylated Derivatives of Isofagomine and Noeuromycin and Their Potential as Inhibitors of β-Glycoside Hydrolases". Australian Journal of Chemistry 60, № 8 (2007): 549. http://dx.doi.org/10.1071/ch07188.

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Анотація:

While isofagomine and noeuromycin have previously been demonstrated to be effective inhibitors of a range of exo-acting glycosidases, they are usually only very weak inhibitors of endo-glycosidases. However, the disaccharide-like 3- and 4-O-β-d-glucopyranosylisofagomines have proven to be strong inhibitors of these endo-acting enzymes that utilize multiple sub-sites. In an attempt to emulate these successes, we have prepared 3- and 4-O-β-d-glucopyranosylnoeuromycin, the former by a selective glycosylation (at O2) of benzyl 4-C-cyano-4-deoxy-α-d-arabinoside (also leading to another synthesis of 3-O-β-d-glucopyranosylisofagomine), the latter by a non-selective glycosylation of benzyl 4-O-allyl-β-l-xyloside with subsequent introduction of the required nitrile group (also leading to another synthesis of 4-O-β-d-glucopyranosylisofagomine). 3-O-β-d-Glucopyranosylnoeuromycin was evaluated as an inhibitor of a family 26 lichenase from Clostridium thermocellum, and 4-O-β-d-glucopyranosylnoeuromycin as an inhibitor of both a family 5 endo-glucanase from Bacillus agaradhaerans and a family 10 endo-xylanase from Cellulomonas fimi. We also report X-ray structural investigations of 3- and 4-O-β-d-glucopyranosylnoeuromycin in complex with the family 26 and family 5 β-glycoside hydrolases, respectively. The two d-glucosylated noeuromycins were indeed able to harness the additional binding energy from the sub-sites of their endo-glycoside hydrolase targets, and were thus excellent inhibitors (in the nanomolar range), binding as expected in the –1 and –2 sub-sites of the enzymes.

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33

Vilotijevic, Ivan, and Timothy Jamison. "Synthesis of Marine Polycyclic Polyethers via Endo-Selective Epoxide-Opening Cascades." Marine Drugs 8, no. 3 (March 19, 2010): 763–809. http://dx.doi.org/10.3390/md8030763.

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34

Armbrust, Kurt W., Matthew G. Beaver, and Timothy F. Jamison. "Rhodium-Catalyzed Endo-Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin." Journal of the American Chemical Society 137, no. 21 (May 18, 2015): 6941–46. http://dx.doi.org/10.1021/jacs.5b03570.

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35

Meza-León, Rosa L., David Crich, Sylvain Bernès, and Leticia Quintero. "Endo-Selective Quenching of Hexahydropyrrolo[2,3-b]indole-BasedN-Acyliminium Ions." Journal of Organic Chemistry 69, no. 11 (May 2004): 3976–78. http://dx.doi.org/10.1021/jo049757p.

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36

Pawar, Prashant, Sagar Vaishampayan, Dinesh H. Shah, and Ameya Pai. "Retro-auricular endo assisted selective neck dissection (how I do it)." Oral Oncology 110 (November 2020): 104942. http://dx.doi.org/10.1016/j.oraloncology.2020.104942.

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37

Aoki, Yoshifumi, Ken Ohmori, and Keisuke Suzuki. "Dioxanone-Fused Dienes Enable Highly Endo-Selective Intramolecular Diels–Alder Reactions." Organic Letters 17, no. 11 (May 14, 2015): 2756–59. http://dx.doi.org/10.1021/acs.orglett.5b01172.

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38

Pradal, Alexandre, Alexandre Nasr, Patrick Y. Toullec, and Veronique Michelet. "Room-Temperature Metal-Free Electrophilic5-endo-Selective Iodocarbocyclization of 1,5-Enynes." Organic Letters 12, no. 22 (November 19, 2010): 5222–25. http://dx.doi.org/10.1021/ol102257z.

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39

Shen, Cong, Yuhang Zhu, Shuqi Jin, Kejie Xu, Shuxin Luo, Lixia Xu, Guofu Zhong, Liangjun Zhong, and Jian Zhang. "Regio- and stereo-selective olefinic C–H functionalization of aryl alkenes in ethanol." Organic Chemistry Frontiers 9, no. 4 (2022): 989–94. http://dx.doi.org/10.1039/d1qo01676h.

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Анотація:

We report on α- and β-olefinic C–H alkenylation of 2-alkenyl benzylamine/benzoic acid derivatives in ethanol to afford aryl dienes/trienes with excellent selectivities, proceeding through 6-/7-membered exo-/endo-cyclometallation.

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40

Emmaniel Raju, Chittala, Veerabhushanam Kadiyala, Gottam Sreenivasulu, Perla Bharath Kumar, Balasubramanian Sridhar, and Galla V. Karunakar. "Gold-catalyzed synthesis of 1H-isochromene-4-carbaldehydes via oxidative cascade cyclization." Organic & Biomolecular Chemistry 19, no. 16 (2021): 3634–43. http://dx.doi.org/10.1039/d1ob00066g.

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Анотація:

An efficient gold-catalyzed formation of indenylidene-derived 1H-isochromene-4-carbaldehydes from substituted 1,5,10-triyne-O-silanes was developed via selective oxidation, 1,2-migration, nucleophilic addition and regioselective 5-endo-dig cyclization.

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41

Krake, Everaldo F., and Wolfgang Baumann. "Selective Oxidation of Clopidogrel by Peroxymonosulfate (PMS) and Sodium Halide (NaX) System: An NMR Study." Molecules 26, no. 19 (September 29, 2021): 5921. http://dx.doi.org/10.3390/molecules26195921.

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A selective transformation of clopidogrel hydrogen sulfate (CLP) by reactive halogen species (HOX) generated from peroxymonosulfate (PMS) and sodium halide (NaX) is described. Other sustainable oxidants as well as different solvents have also been investigated. As result of this study, for each sodium salt the reaction conditions were optimized, and four different degradation products were formed. Three products were halogenated at C-2 on the thiophene ring and have concomitant functional transformation, such as N-oxide in the piperidine group. A halogenated endo-iminium product was also observed. With this condition, a fast preparation of known endo-iminium clopidogrel impurity (new counterion) was reported as well. The progress of the reaction was monitored using nuclear magnetic resonance spectroscopy as an analytical tool and all the products were characterized by 1D-, 2D-NMR and HRMS.

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42

Kong, Xiang-Fei, Xiu-Yun Guo, Zi-Yu Gu, Lin-Su Wei, Lu-Lu Liu, Dong-Liang Mo, Cheng-Xue Pan, and Gui-Fa Su. "Silver(i)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles." Organic Chemistry Frontiers 7, no. 15 (2020): 2055–62. http://dx.doi.org/10.1039/d0qo00437e.

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A silver-catalyzed selective 8-endo-dig cyclization of C2-alkynyl quinazolinones was developed to prepare a series of novel quinazolinone-fused eight-membered N,O-heterocycles in good-to-excellent yields under mild reaction conditions.

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43

Zakrzewska, Katerina E., Amanda Sainsbury, Isabelle Cusin, Juha Rouru, Bernard Jeanrenaud, and Françoise Rohner-Jeanrenaud. "Selective Dependence of Intracerebroventricular Neuropeptide Y-Elicited Effects on Central Glucocorticoids*." Endocrinology 140, no. 7 (July 1, 1999): 3183–87. http://dx.doi.org/10.1210/endo.140.7.6874.

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44

Kim, Yong Hae, Sam Min Kim, Doo Han Park, and So Won Youn. "Stereocontrolled asymmetric synthesis." Pure and Applied Chemistry 72, no. 9 (January 1, 2000): 1691–97. http://dx.doi.org/10.1351/pac200072091691.

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Stereo differentiated asymmetric syntheses have been achieved by S-indoline derivations. Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the structures of chiral dienophiles. Diastereo- and enantio-selective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S)- or (R,R)-2,3-dialkyltar-taric acid and derivatives can be synthesized for the first time depending on the structure of α-ketoamides.

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45

Escalante, Carlos H., Eder I. Martínez-Mora, Carlos Espinoza-Hicks, Alejandro A. Camacho-Dávila, Fernando R. Ramos-Morales, Francisco Delgado, and Joaquín Tamariz. "Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole." Beilstein Journal of Organic Chemistry 16 (June 17, 2020): 1320–34. http://dx.doi.org/10.3762/bjoc.16.113.

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A highly regio-, chemo- and stereoselective divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels–Alder and Heck arylation reactions. 3-(N-Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly endo-Diels–Alder cycloaddition with maleimides to furnish octahydropyrrolo[3,4-e]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(N-benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-a]isoindol-3-yl)acrylates. A further oxidative aromatization of the polycyclic intermediates provides the corresponding polycyclic pyrrolo-isoindoles and isoindolo-pyrrolo-indoles. A theoretical study on the stereoselective Diels–Alder reactions, carried out by calculating the endo/exo transition states, revealed the assistance of non-covalent interactions in governing the endo stereocontrol.

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46

Strowski, M. Z., R. M. Parmar, A. D. Blake, and J. M. Schaeffer. "Somatostatin Inhibits Insulin and Glucagon Secretion via Two Receptor Subtypes: An in Vitro Study of Pancreatic Islets from Somatostatin Receptor 2 Knockout Mice*." Endocrinology 141, no. 1 (January 1, 2000): 111–17. http://dx.doi.org/10.1210/endo.141.1.7263.

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Abstract Somatostatin (SST) potently inhibits insulin and glucagon release from pancreatic islets. Five distinct membrane receptors (SSTR1–5) for SST are known, and at least two (SSTR2 and SSTR5) have been proposed to regulate pancreatic endocrine function. Our current understanding of SST physiology is limited by the receptor subtype selectivity of peptidyl SST analogs, making it difficult to assign a physiological function to an identified SST receptor subtype. To better understand the physiology of SSTRs we studied the in vitro effects of potent subtype-selective nonpeptidyl SST analogs on the regulation of pancreatic glucagon and insulin secretion in wild-type (WT) and in somatostatin receptor 2 knockout (SSTR2KO) mice. There was no difference in basal glucagon and insulin secretion between islets isolated from SSTR2KO and WT mice; however, potassium/arginine-stimulated glucagon secretion was approximately 2-fold higher in islets isolated from SSTR2KO mice. Neither SST nor any SSTR-selective agonist inhibited basal glucagon or insulin release. SST-14 potently inhibited stimulated glucagon secretion in islets from WT mice and much less effectively in islets from SSTR2KO mice. The SSTR2 selective analog L-779,976 inhibited glucagon secretion in islets from WT, but was inactive in islets from SSTR2KO mice. L-817,818, an SSTR5 selective analog, slightly reduced glucagon release in both animal groups, whereas SSTR1, -3, and -4 selective analogs were inactive. SST and L-817,818 inhibited glucose stimulated insulin release in islets from WT and SSTR2KO mice. L-779,976 much less potently reduced insulin secretion from WT islets. In conclusion, our data demonstrate that SST inhibition of glucagon release in mouse islets is primarily mediated via SSTR2, whereas insulin secretion is regulated primarily via SSTR5.

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47

Li, Lei, William L. Turnbull, Robert McDonald, and F. G. West. "Lithium Hydroxide Assisted Endo ‐Selective [4+4]‐Photocycloaddition of Pyran‐2‐ones." European Journal of Organic Chemistry 2021, no. 16 (April 9, 2021): 2294–300. http://dx.doi.org/10.1002/ejoc.202100122.

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48

Yamada, Tohru, Tomoko Ashizawa, Natsuki Ohtsuki, Tomoyuki Miura, Makoto Ohya, Takaomi Shinozaki, and Taketo Ikeno. "Endo-Selective Asymmetric Inverse Electron-Demand 1,3-Dipolar Cycloaddition Reaction of Nitrones." HETEROCYCLES 68, no. 9 (2006): 1801. http://dx.doi.org/10.3987/com-06-10791.

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49

Sarkar, Amitabha, Sambasivam Ganesh, Surojit Sur, Sunil K. Mandal, Vishwanath M. Swamy, Bikash C. Maity, and Tipparaju Suresh Kumar. "Contra-intuitive stereocontrol: endo-selective nucleophilic additions on an arene–tricarbonylchromium template." Journal of Organometallic Chemistry 624, no. 1-2 (April 2001): 18–25. http://dx.doi.org/10.1016/s0022-328x(00)00836-6.

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50

Karcher, Thomas, Willi Sicking, Jürgen Sauer, and Reiner Sustmann. "Solvent effects on endo/exo selective in (4 + 2) cycloadditions of cyanoethylenes." Tetrahedron Letters 33, no. 52 (December 1992): 8027–30. http://dx.doi.org/10.1016/s0040-4039(00)74708-3.

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