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Journal articles on the topic 'Cyclopenta-1'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Campbell, M., DJ Collins, and AM James. "Synthesis of 2-(5',5'-Ethylenedioxy-1'-methylcyclopent-2'-en-1'-yl)ethanol, and Some 2H-Cyclopenta[b]furan Derivatives Formed by Intramolecular Displacement Reactions." Australian Journal of Chemistry 42, no. 1 (1989): 17. http://dx.doi.org/10.1071/ch9890017.

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Exchange dioxolanation of 2-methyl-2-(prop-2′-enyl)cyclopentane-1,3-done (1b) gave 3,3- ethylenedioxy-2-methyl-2-(prop-2′-enyl) cyclopentan-1-one (2) which, upon reduction and esterification , afforded the epimeric 3,3-ethylenedioxy-2-methyl-2-(prop-2′-enyl) cyclopent-1-yl benzoates (6d). Oxidative cleavage of the terminal double bond in (6d),followed by sodium borohydride reduction yielded 3,3-ethylenedioxy-2-(2'-hydroxyethyl)-2-methylcyclopent-1-yl benzoate (4b) which underwent acid- catalysed rearrangement to 6a-(2′-hydroxyethoxy)-3a- methylhexahydrocyclopenta [b]furan-4-yl benzoate (8b). Flash vacuum pyrolysis of the t- butyldimethylsilyl ether (12), derived from the hydroxy acetal (4b), afforded 3-[2′- (t- butyldimethylsilyloxy )ethyl]-4,4-ethy1enedioxy-3-methylcyclopent-1-ene (14) which upon selective cleavage of the silyl ether group gave 2-(5′,5′-ethylenedioxy-1′-methylcyclopent- 2'′en-1′-y1)ethanol (7). Reaction of the mesylate (16) of (7) with lithium bromide or iodide in tetrahydrofuran at 50-55� for several hours yielded some of the corresponding 3-(2′-haloethyl) compounds (17), but gave mainly the rearranged 6a-(2′-haloethoxy)-3a-methyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furans (19a) and (19b). Some related chemistry is described.

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2

Gataullin, Rail R., Ekaterina S. Mescheryakova, Rifkat M. Sultanov, Akhnef A. Fatykhov, and Leonard M. Khalilov. "An Unexpected Dihalogenation/Dehydrogenation Product Derived via Iodolactonization of an N-Tosyl-N-[6-(2-cyclopenten-1-yl)-2-methylphenyl]glycine." Synthesis 51, no. 18 (June 19, 2019): 3485–90. http://dx.doi.org/10.1055/s-0039-1689971.

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The reaction between N-tosyl-N-[6-(2-cyclopenten-1-yl)phenyl]glycine (syn/anti atropisomeric mixture) and molecular iodine is studied. Along with the expected 8-exo-cyclization product possessing a 3-iodo-2,3,3a,6,7,11b-hexahydrobenzo[e]cyclopenta[g][1,4]oxazocine core, the unexpected 1,11b-dehydrogenated/1-iodinated analogue with a 1,3-diiodo-3,3a,6,7-tetrahydrobenzo[e]cyclopenta[g][1,4]oxazocine structure is observed for the first time in a conventional halolactonization reaction.

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3

Kotha, Sambasivarao, and Yellaiah Tangella. "Modular Approaches to Cyclopentanoids and their Heteroanalogs." Synlett 31, no. 20 (October 12, 2020): 1976–2012. http://dx.doi.org/10.1055/a-1288-8240.

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AbstractCyclopentanoids and their derivatives are interesting targets in synthetic organic chemistry due to their extensive applications in various branches of chemical sciences like pharmaceuticals, natural and non-natural products. In view of these applications, several synthetic strategies have been developed in the past three to four decades. In this article, we describe our work towards the synthesis of cyclopentanoids and their heteroanalogs involving diverse synthetic strategies during the past two decades. Among these, photo-thermal olefin metathesis, ring-closing metathesis, ring-rearrangement metathesis, cyclopentane annulation, [2+2+2] cycloaddition and Diels–Alder reactions have been used to assemble cyclopentane rings of diverse architecture. 1 Introduction 2 Synthesis of Spiro[4.4]nonane (A1) Derivatives 3 Synthesis of Octahydropentalene (A2) Derivatives 4 Synthesis of Linear Triquinanes (A3) 5 Synthesis Spiro Triquinanes (A4) 6 Synthesis of Angular Triquinane (A5) Systems 7 Synthesis of Hexahydro-2′H-spiro[cyclopentane-1,1′-pentalene] (A6) Ring System 8 Synthesis of Dispiro[4.1.47.25]tridecane (A7) Ring System 9 Synthesis of Hexahydro-1H-3a,7a-propanoindene Ring System10 Synthesis of Linear Tetraquinanes (A11 and A12)11 Synthesis of Tetrahydro-1′H,3′H-dispiro[cyclopentane-1,2′-pentalene-5′,1′′-cyclopentane] (A13) Ring System12 Synthesis of Decahydro-1H,8H-dicyclopenta[a,h]pentalene (A14) Ring System13 Synthesis of Dodecahydro-1H-dicyclopenta[a,d]pentalene (A15) Ring System14 Synthesis of Octahydro-1′H-spiro[cyclopentane-1,2′-cyclopenta[c]pentalene] (A16) Ring System15 Synthesis of Decahydrospiro[cyclopentane-1,7′-cyclopenta-[a]pentalene] (A17) Ring System16 Synthesis of Compact Tetraquinane (A18)17 Synthesis of Higher Polyquinanes18 Conclusions19 Acronyms

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4

Si, Mrinal Kanti, and Bishwajit Ganguly. "A DFT study to design super- and hyperacids with 1-(cyclopenta-2,4-dien-1-yl)-4-nitrobenzene and 3-(cyclopenta-2,4-dien-1-ylmethylene)-6-methylenecyclohexa-1,4-diene molecules." New Journal of Chemistry 41, no. 4 (2017): 1425–29. http://dx.doi.org/10.1039/c6nj03529a.

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DFT calculations reveal that poly-cyano-substituted 1-(cyclopenta-2,4-dien-1-yl)-4-nitrobenzene and 3-(cyclopenta-2,4-dien-1-ylmethylene)-6-methylenecyclohexa-1,4-diene can function as super- to hyper-acids.

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5

Peipiņš, Uldis, Niks Freimanis, Dmitrijs Stepanovs, Anatoly Mishnev, and Māris Turks. "Betulin 3,28-di-O-tosylate." Acta Crystallographica Section E Structure Reports Online 70, no. 8 (July 23, 2014): o879—o880. http://dx.doi.org/10.1107/s1600536814016602.

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The title compound, C44H62O6S2{systematic name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-[(tosyloxy)methyl]icosahydro-1H-cyclopenta[a]chrysen-9-yl 4-methylbenzenesulfonate}, was obtained by tosylation of naturally occurring betulin. All the cyclohexane rings adopt chair conformations and the cyclopentane ring adopts a twisted envelope conformation, with the C atom bearing the tosylmethyl substituent forming the flap. In the crystal, molecules form a three-dimensional network through multiple weak C—H...O hydrogen bonds.

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6

Çelik, Ísmail, Mehmet Akkurt, Ahmet Tutar, Ramazan Erenler, and Santiago García-Granda. "2,3-Dihydro-1H-cyclopenta[b]naphthalen-1-ol." Acta Crystallographica Section E Structure Reports Online 68, no. 3 (February 10, 2012): o687. http://dx.doi.org/10.1107/s1600536812005181.

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7

Wardakhan, Wagnat Wahba, El-Sayed Nahed Nasser Eid, and Rafat Milad Mohareb. "Synthesis and anti-tumor evaluation of novel hydrazide and hydrazide-hydrazone derivatives." Acta Pharmaceutica 63, no. 1 (March 1, 2013): 45–57. http://dx.doi.org/10.2478/acph-2013-0004.

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The reaction of cyclopentanone with cyanoacetylhydrazine gave 2-cyano-2-cyclopentylideneacetohydrazide (1). Treatment of compound 1 with elemental sulphur in the presence of triethylamine afforded 2-amino-5,6-dihydro- -4H-cyclopenta[b]thiophene-3-carbohydrazide (2), which in-turn formed the corresponding intermediate diazonium salt. The latter was coupled with either ethyl cyanoacetate or ethyl acetoacetate to form 2-cyano-2-(3-(hydrazinecarbonyl)- 5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)hydrazono) acetate (3) and ethyl 2-(2-(3-(hydrazinecarbonyl)-5,6-dihydro- 4H-cyclopenta[b]thiophen-2-yl)hydrazono)-3-oxobutanoate (4), respectively. On the other hand, the reaction of compound 1 with either benzaldehyde or acetophenone afforded N’-benzylidene-2-cyano-2-cyclopentylideneacetohydrazide (7) and 2-cyano-2-(2-cyclopentylidene)phenylacetohydrazide (10), respectively. Moreover, compound 1 was used to synthesize 2-cyano-2-cyclopentylidene- N'-(arylthiazol-2(3H)-ylidene)acetohydrazides (6a,b), 2-(2-benzylidenecyclopentylidene)-2-cyanoacetohydrazide (8), 2-amino-N'-benzylidene-5,6-dihydro-4H- -cyclopenta[b]thiophene-3-carbohydrazide (9), 2-cyano- -2-(2-(2-phenylhydrazono)cyclopentylidene)acetohydrazide (11), N'-(1-chloropropan-2-ylidene)-2-cyano-2-cyclopentylideneacetohydrazide (12), and 2-cyclopentylidene-3- -(3,5-disubstituted-1H-pyrazol-1-yl)-3-oxopropanenitriles (13a,b) through its reaction with the respective reagents. Antitumor evaluation of the newly synthesized compounds against the three human tumor cells lines, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) showed that some of the described compounds exhibited higher inhibitory effects towards the three tumor cell lines than the reference compound doxorubicin.

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8

Gelbrich, Thomas, Volker Kahlenberg, Christoph Langes, and Ulrich J. Griesser. "Telaprevir: helical chains based on three-point hydrogen-bond connections." Acta Crystallographica Section C Crystal Structure Communications 69, no. 2 (January 16, 2013): 179–82. http://dx.doi.org/10.1107/s0108270113000954.

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The crystal structure of the title compound [systematic name: (1S,3aR,6aS)-2-((2S)-2-{[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino}-3,3-dimethylbutanoyl)-N-[(3S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-1-carboxamide], C36H53N7O6, contains two independent molecules, which possess distinct conformations and a disordered cyclopenta[c]pyrrolidine unit. In the crystal, molecules are linked into helical chainsviathree-point N—H...O hydrogen-bond connections in which three NH and three carbonyl groups per molecule are utilized. The chiralities of the six stereocentres per molecule inferred from this study are in agreement with the synthetic procedure.

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9

Christensen, Torben Bo, Karl Anker Jørgensen, Finn Krebs Larsen, Lars Martiny, Jørgen Møller, Alexander Senning, and Lucia Vichi. "Formation of a 4H-cyclopenta-1,2,3-thiadiazole by rearrangement of a transient N-(thionitroso)cyclopenta-2,4-diene-1-imine." J. Chem. Soc., Chem. Commun., no. 6 (1993): 489–91. http://dx.doi.org/10.1039/c39930000489.

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10

Huo, Fang-Jun, Cai-Xia Yin, and Pin Yang. "7-Nitro-2,3-dihydro-1H-cyclopenta[b]chromen-1-one." Acta Crystallographica Section E Structure Reports Online 60, no. 11 (October 22, 2004): o2087—o2089. http://dx.doi.org/10.1107/s1600536804026078.

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11

Zhang, Liang, Di Sun, Xiang-Zhi Gao, Su-Yuan Xie, and Rong-Bin Huang. "5-Bromo-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-one." Acta Crystallographica Section E Structure Reports Online 65, no. 9 (August 19, 2009): o2174. http://dx.doi.org/10.1107/s1600536809031547.

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12

Radeglia, B., and B. Wagner. "Protonenmagnetische Resonanzspektren von Methylderivaten des Isothialens (Cyclopenta[c]thiopyran) [1]." Zeitschrift für Chemie 4, no. 4 (September 2, 2010): 145. http://dx.doi.org/10.1002/zfch.19640040405.

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13

Kim, Jinwoo, Youngeup Jin, Suhee Song, Il Kim, and Hongsuk Suh. "Synthesis of 4H-Cyclopenta[def]phenanthrene from 1-Naphthylacetic Acid." Chemistry Letters 38, no. 10 (October 5, 2009): 1008. http://dx.doi.org/10.1246/cl.2009.1008.

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14

Huo, Fangjun, Caixia Yin, and Pin Yang. "7-Methoxy-2,3-dihydro-1H-cyclopenta[b]chromen-1-one." Acta Crystallographica Section E Structure Reports Online 60, no. 12 (November 13, 2004): o2278—o2280. http://dx.doi.org/10.1107/s1600536804028478.

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15

Lippmann, Eberhard, and Bernd Gärtner. "Versuche zur Darstellung von 1-Oxo-2,3-dihydro-1 H-cyclopenta[b]chinoxalin." Zeitschrift für Chemie 11, no. 2 (September 1, 2010): 62. http://dx.doi.org/10.1002/zfch.19710110207.

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16

Diao, Yunxia, Zhijun Zuo, Hui Wang, Jingjing Liu, and Xinjun Luan. "Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers." Organic & Biomolecular Chemistry 15, no. 21 (2017): 4601–8. http://dx.doi.org/10.1039/c7ob00768j.

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17

Harrison, Carrie-Ann, Ralf Leineweber, Christopher J. Moody, and Jonathan M. J. Williams. "Cyclopenta[b]indoles. Part 1. Synthesis of cyclopenta[b]indoles by formal [3 + 2] addition of indolylmethyl cations to alkenes." Journal of the Chemical Society, Perkin Transactions 1, no. 9 (1995): 1127. http://dx.doi.org/10.1039/p19950001127.

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18

Kozmík, Václav, and Jaroslav Paleček. "Synthetic Analogues of Prostaglandins F2α and E2." Collection of Czechoslovak Chemical Communications 59, no. 1 (1994): 138–48. http://dx.doi.org/10.1135/cccc19940138.

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The synthesis of new derivatives of prostaglandins F2α and E2 XIIa,b - XVa,b and XXa,b - XXIIIa,b containing the furan or thiophene nucleus in the upper chain has been accomplished starting from [3aα,4α,5β,6aα]-(±)-hexahydro-5-hydroxy-4-((E)-(3α)-hydroxy-1-octenyl)-2H-cyclopenta[b]furan-2-one (Ia) and [3aα,4α,5β,6aα]-(±)-hexahydro-5-hydroxy-4-[4-(3-chlorophenoxy)-(3α)-hydroxy-1-butenyl]cyclopenta[b]furan-2-one (Ib). The diols Ia and Ib have been converted into the above-mentioned analogues of prostaglandins F2α and E2 by protecting the hydroxyl groups, subsequent reduction and Wittig reaction with the ylides prepared from the phosphonium salts IV - VII, and final deprotection (or oxidation plus deprotection).

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19

Hussain, Altaf, Hamid Latif Siddiqui, Rehana Rashid, Khalid Mehmood Khan, and Masood Parvez. "1-(5a,5b,8,8,11a,13b-Hexamethyleicosahydro-1H-cyclopenta[a]chrysen-3-yl)-1-ethanone." Acta Crystallographica Section E Structure Reports Online 64, no. 4 (March 20, 2008): o723. http://dx.doi.org/10.1107/s1600536808006831.

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20

Sun, Qi, Wanli Nie, and Maxim V. Borzov. "2-[(Cyclopenta-1,3-dien-2-yl)diphenylmethyl]-1-methyl-1H-imidazole." Acta Crystallographica Section E Structure Reports Online 66, no. 2 (January 9, 2010): o285—o286. http://dx.doi.org/10.1107/s1600536809055561.

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21

CHRISTENSEN, T. B., K. A. JOERGENSEN, F. K. LARSEN, L. MARTINY, J. MOELLER, A. SENNING, and L. VICHI. "ChemInform Abstract: Formation of a 4H-Cyclopenta-1,2,3-thiadiazole by Rearrangement of a Transient N-(Thionitroso)cyclopenta-2,4-dien-1-imine." ChemInform 24, no. 32 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199332170.

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22

Zhang, Mi, Shan Yan, Yu Liang, Meijia Zheng, Zhaodi Wu, Yi Zang, Muyuan Yu, et al. "Talaronoids A–D: four fusicoccane diterpenoids with an unprecedented tricyclic 5/8/6 ring system from the fungus Talaromyces stipitatus." Organic Chemistry Frontiers 7, no. 21 (2020): 3486–92. http://dx.doi.org/10.1039/d0qo00960a.

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Talaronoids A–D (1–4), four fusicoccane diterpenoids with an unexpected tricyclic 5/8/6 carbon skeleton from Talaromyces stipitatus, represent the first examples of natural products with a benzo[a]cyclopenta[d]cyclooctane skeleton.

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23

Li, Renlong, Gongchu Liu, Ruihao Xie, Zhenfeng Wang, Xiye Yang, Kang An, Wenkai Zhong, et al. "Introducing cyclic alkyl chains into small-molecule acceptors for efficient polymer solar cells." Journal of Materials Chemistry C 6, no. 26 (2018): 7046–53. http://dx.doi.org/10.1039/c8tc01780h.

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A new acceptor–donor–acceptor type small molecule acceptor, namely IDT-HN, is developed, which consists of a newly developed 2-(3-oxo-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile as the peripheral electron-withdrawing group.

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24

Banerjee, Sanjib, Bhausaheb V. Tawade, and Bruno Améduri. "Functional fluorinated polymer materials and preliminary self-healing behavior." Polymer Chemistry 10, no. 16 (2019): 1993–97. http://dx.doi.org/10.1039/c9py00122k.

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Effective use of Diels–Alder chemistry led to the development of thermally amendable and self-healing polymeric materials based on a copolymer of cyclopenta-1,3-dien-1-ylmethyl 2-(trifluoromethyl)acrylate (MAF-Furan) and 2,2,2-trifluoroethyl α-fluoroacrylate (FATRIFE).

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25

HARRISON, C. A., R. LEINEWEBER, C. J. MOODY, and J. M. J. WILLIAMS. "ChemInform Abstract: Cyclopenta(b)indoles. Part 1. Synthesis of Cyclopenta(b)indoles by Formal (3 + 2) Addition of Indolylmethyl Cations to Alkenes." ChemInform 26, no. 36 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199536143.

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26

Luo, Qi, Zhen Wang, Jin-Feng Luo, Zheng-Chao Tu, and Yong-Xian Cheng. "(±)-Applanatumines B–D: novel dimeric meroterpenoids from Ganoderma applanatum as inhibitors of JAK3." RSC Advances 7, no. 60 (2017): 38037–43. http://dx.doi.org/10.1039/c7ra04862a.

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Applanatumines B–D (1–3), three pairs of dimeric meroterpenoid enantiomers featuring the presence of a 6-oxo-4,4a,5,5a,6,8,8a,8b-octahydrofuro[3′,4′:4,5]cyclopenta[1,2-b]pyran-3-carbaldehyde structure core, were isolated from the fruiting bodies of Ganoderma applanatum.

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27

Wagner, R., and R. Mayer. "Schwefel-Heterocyclen, XII [1] Isothialene (Cyclopenta[c] thiapyrane) aus Cyclopentadien und Thiazolen." Zeitschrift für Chemie 3, no. 1 (September 2, 2010): 25–26. http://dx.doi.org/10.1002/zfch.19630030106.

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28

Li, Shuhong. "1′,3′,4′,5′,7′,8′-Hexafluoro-1,1′′,2,2′′,3,3′′,4,4′′-octaphenyl-2′,6′-dihydrodispiro[cyclopenta-1,3-diene-5,2′-naphthalene-6′,5′′-cyclopenta-1′′,3′′-diene] dichloromethane monosolvate." Acta Crystallographica Section E Structure Reports Online 67, no. 8 (July 30, 2011): o2208. http://dx.doi.org/10.1107/s1600536811030285.

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29

Wang, Ye, Yang Yuan, Zongkang Wang, Yingge Gu, Siyi Fu, Lingkai Kong, and Yanzhong Li. "Silver-Mediated [2 + 2 + 1] Cyclization Reaction of Diynes with Elemental Selenium/Sulfur To Synthesize 3,4-Substituted Cyclopenta[c]selenophenes/Cyclopenta[c]thiophenes." Organic Letters 23, no. 15 (July 20, 2021): 5911–16. http://dx.doi.org/10.1021/acs.orglett.1c02018.

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30

Subba Reddy, B. V., Y. Vikram Reddy, and Kiran Kumar Singarapu. "Sequential aza-Piancatelli rearrangement/Friedel–Crafts alkylation for the synthesis of pyrrolo[1,2-d]benzodiazepine derivatives." Organic & Biomolecular Chemistry 14, no. 3 (2016): 1111–16. http://dx.doi.org/10.1039/c5ob01616a.

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2-Furylcarbinols undergo a smooth aza-Piancatelli rearrangement followed by Friedel–Crafts alkylation with (1H-pyrrol-1-yl)aniline, in the presence of In(OTf)₃ at room temperature to afford the corresponding hexahydrobenzo[b]cyclopenta[f]pyrrolo[1,2-d][1,4]diazepin-11(4aH)-one scaffolds.

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31

Lee, Eun Kyeong, Ju Hyun Kim, Kyoung Mi Moon, Sugyeong Ha, Sang-Gyun Noh, Dae Hyun Kim, Bonggi Lee, et al. "Tyrosinase Inhibitory Effect of (E)-2-(substituted benzylidene)-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-one Derivatives." Journal of Life Science 27, no. 2 (February 28, 2017): 139–48. http://dx.doi.org/10.5352/jls.2017.27.2.139.

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32

Ivanova, N. A., V. A. Akhmetyanova, N. P. Akhmetdinova, O. V. Shitikova, K. Yu Suponitzky, and M. S. Miftakhov. "Synthesis of enantiomeric (+)- and (-)-6-(1-methylethylidene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-1-ones." Russian Journal of Organic Chemistry 50, no. 6 (June 2014): 810–14. http://dx.doi.org/10.1134/s1070428014060098.

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33

Yang, Guan-Jun, Chung-Nga Ko, Hai-Jing Zhong, Chung-Hang Leung, and Dik-Lung Ma. "Structure-Based Discovery of a Selective KDM5A Inhibitor that Exhibits Anti-Cancer Activity via Inducing Cell Cycle Arrest and Senescence in Breast Cancer Cell Lines." Cancers 11, no. 1 (January 15, 2019): 92. http://dx.doi.org/10.3390/cancers11010092.

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Breast cancer is the one of the most frequent causes of female cancer mortality. KDM5A, a histone demethylase, can increase the proliferation, metastasis, and drug resistance of cancers, including breast cancer, and is thus an important therapeutic target. In the present work, we performed hierarchical virtual screening towards the KDM5A catalytic pocket from a chemical library containing 90,000 compounds. Using multiple biochemical methods, the cyclopenta[c]chromen derivative 1 was identified as the top candidate for KDM5A demethylase inhibitory activity. Compared with the well-known KDM5 inhibitor CPI-455 (18), 1 exhibited higher potency against KDM5A and much higher selectivity for KDM5A over both KDM4A and other KDM5 family members (KDM5B and KDM5C). Additionally, compound 1 repressed the proliferation of various KDM5A-overexpressing breast cancer cell lines. Mechanistically, 1 promoted accumulation of p16 and p27 by blocking KDM5A-mediated H3K4me3 demethylation, leading to cell cycle arrest and senescence. To date, compound 1 is the first cyclopenta[c]chromen-based KDM5A inhibitor reported, and may serve as a novel motif for developing more selective and efficacious pharmacological molecules targeting KDM5A. In addition, our research provides a possible anti-cancer mechanism of KDM5A inhibitors and highlights the feasibility and significance of KDM5A as a therapeutic target for KDM5A-overexpressing breast cancer.

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34

Thirunarayanan, Ganesamoorthy, and K. G. Sekar. "Solvent-Free Synthesis and Spectral Linearity of Some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta[b]thiophene-3-carboxamides." International Letters of Chemistry, Physics and Astronomy 13 (September 2013): 160–74. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.13.160.

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Some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta[b]thiophene-3-carboxamide derivatives have been synthesized by SiO2:H3PO4 catalyzed solvent-free condensation of 2-amino-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta [b]thiophene-3-carboxamide and various substituted benzaldehydes in microwave irradiation. The yield of the imine-carboximido derivatives has been found to be more than 85 %. The purity of all imine-carboximido derivatives has been checked using their physical constants and spectral data. The spectral data of the imine-carboximido derivatives such as infrared ν (cm-1) of CO, NH, C-N, C-Cl, C-F, C=N, and the NMR chemical shifts (δ, ppm) of NH, CH, CO and C=N have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analysis, the effects of substituent on the above spectral group absorptions have been discussed.

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35

Curran, Dennis P., and Hui Liu. "4 + 1 Radical annulations with isonitriles: a simple route to cyclopenta-fused quinolines." Journal of the American Chemical Society 113, no. 6 (March 1991): 2127–32. http://dx.doi.org/10.1021/ja00006a033.

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36

Türker, Lemi, Yılmaz Yıldırır, and Serkan Yavuz. "Quantum chemical studies on some 1-selena-cyclopenta[b]naphthalene-3-one derivatives." Journal of Molecular Structure: THEOCHEM 673, no. 1-3 (March 2004): 35–41. http://dx.doi.org/10.1016/j.theochem.2003.11.036.

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37

Odabaşoğlu, M., and O. Büyükgüngör. "2,3-Dibromo-3aH,5H-4-oxa-9b-aza-cyclopenta[a]naphthalene-1-one." Acta Crystallographica Section A Foundations of Crystallography 68, a1 (August 7, 2012): s257. http://dx.doi.org/10.1107/s0108767312095001.

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38

Sankaranarayanan, R., D. Velmurugan, S. Shanmuga Sundara Raj, Hoong-Kun Fun, G. Babu, and P. T. Perumal. "4-[1-(Phenylsulfonyl)indol-3-yl]-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline." Acta Crystallographica Section C Crystal Structure Communications 56, no. 4 (April 15, 2000): 475–76. http://dx.doi.org/10.1107/s0108270100000640.

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39

Balo, Carmen, Carmen López, Olga Caamaño, Franco Fernández, Xerardo García-Mera, and José Enrique Rodríguez-Borges. "Synthesis of Novel Purinyl-1′-homocarbanucleosides Based on a Cyclopenta[b]pyrazine System." CHEMICAL & PHARMACEUTICAL BULLETIN 56, no. 5 (2008): 654–58. http://dx.doi.org/10.1248/cpb.56.654.

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40

Yufit, D. S., and Yu T. Struchkov. "Crystal and molecular structure of 1,2,3,4,5-pentachloro-1-(2,5-dioxanyl)cyclopenta-2,4-diene." Journal of Structural Chemistry 28, no. 1 (1987): 153–55. http://dx.doi.org/10.1007/bf00749569.

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41

Conti, Giuseppe, Guillermo Arribas, Angelina Altomare, Bernardo Mendez, and Francesco Ciardelli. "Synthesis, Characterization and Monoalkene Polymerization Activity of Bis-[(1,2,3,4-tetraphenyl)-η5-cyclopentadienyl]zirconium(IV) Dichloride." Zeitschrift für Naturforschung B 50, no. 3 (March 1, 1995): 411–14. http://dx.doi.org/10.1515/znb-1995-0315.

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The title complex (1) has been prepared by reaction of ZrCl4 with 1,2,3,4-(tetraphenyl)- cyclopenta-1,3-dienyl lithium (2). The phenyl substituents on the metallocene ligands exert both steric and electronic effects on the active site obtained by activation of 1 with MAO. Thus this catalytic system shows lower polymerization activity than in case of unsubstituted or methyl-substituted ligands and leads to the formation of ethylene oligomers.

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42

Ceylan, Mustafa, Seher Yalçın, Hasan Seçen, Yaşar Sütbeyaz, and Metin Balci. "Evidence for the formation of a New Five-Membered Ring Cyclic Allene: Generation of 1-Cyclopenta-1,2-Dien-1-Ylbenzene." Journal of Chemical Research 2003, no. 1 (January 2003): 21–23. http://dx.doi.org/10.3184/030823403103172797.

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Treatment of 1-(2-iodocyclopent-1-en-1-yl)benzene (13), dissolved in benzene, with potassium t-butoxide resulted in the formation of 1-(2-phenylcyclopent-1-en-1-yl)benzene (15) and 1-cyclopent-1-en-1-ylbenzene (5) in a ratio of 1:1.

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43

Byrne, Lindsay T., Manat Phomakotr, Chompoonut Poolsanong, Vichai Reutrakul, Brian W. Skelton, and Allan H. White. "α-Sulfonyl Radical Initiated Intramolecular Tandem Radical Cyclization: Stereochemistries of a Pair of Doubly Cyclized Products." Australian Journal of Chemistry 56, no. 7 (2003): 715. http://dx.doi.org/10.1071/ch02134.

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Room-temperature single-crystal X-ray structure determinations are recorded for trans-1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]-1-benzothiapyran-4,4-dioxide and its 3a-methyl analogue, minor products of the α-sulfonyl radical-initiated intramolecular tandem radical cyclization of H2C=CH(CH2)CRBrSO2Ph (R = H, CH3), confirming the assigned structures and rigorously establishing the trans relationship at the ring junctions.

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44

Nokami, Junzo, Kazuhiko Fujii, Yusuke Mizutani, Rikiya Omatsu, Kiyoshi Watanabe, Hiroshi Yasuda, and Tsutomu Inokuchi. "Cyclopentanoids from Cyclopentadiene: Synthesis of (-)-Methyl jasmonate and (+)-12-Oxophytodienoic acid." Natural Product Communications 8, no. 7 (July 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800716.

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Linoleic acid metabolites (-)-methyl jasmonate and (+)-12-oxophytodienoic acid ((+)-12-oxo-PDA) were prepared from the same precursor (1,2-trans, 1,3- cis, 2′ Z)-2-(pent-2′-enyl)-cyclopent-4-en-1,3-diol which was obtained by regioselective pent-2-enylation of cyclopentadiene and following photooxidation to cis −1,3-diol. A methoxycarbonylmethyl substituent was introduced to the cyclopentane ring via alkylation of the π-allyl palladium intermediate derived from (1 R,2 S,3 S,2′ Z)-3-acetoxy-2-(pent-2′-enyl)cyclopent-4-ene-1-ol with dimethyl malonate for (-)-methyl jasmonate. The α-chain was introduced to the cyclopentane ring via the SN2 type nucleophilic substitution of (1 S,2 R,3 R,2′ Z)-3-acetoxy-2-(pent-2′-enyl)cyclopent-4-ene-1-ol with a dialkylcuprate for (+)-12-oxo-PDA.

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45

Prakash, Meher, Rajni Lodhi, and Sampak Samanta. "Substrate-Controlled Domino Reaction of N-Sulfonyl Ketimines with 2-Aroyl-1-chlorocyclopropanecarboxylates: Access to Cyclopenta[c]chromenes and Benzo[f]cyclopenta[d][1,2]thiazepine Dioxides." Journal of Organic Chemistry 86, no. 9 (April 12, 2021): 6721–33. http://dx.doi.org/10.1021/acs.joc.1c00459.

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46

Fotie, Jean, Chris F. Fronczek, Kyle A. Burns, Frank R. Fronczek, Cheryl Bain, D. Scott Bohle, and Ferdinand P. Poudeu. "4-(8-Ethoxy-2,3-dihydro-1H-cyclopenta[c]quinolin-4-yl)butane-1-peroxol." Acta Crystallographica Section E Structure Reports Online 66, no. 7 (June 16, 2010): o1660. http://dx.doi.org/10.1107/s1600536810021781.

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47

Odabasoglu, M., and O. Buyukgungor. "Structure of dihydro-isoindolo benzoxazine-11-one and dibromo-cyclopenta[a]naphthalene-1-one." Acta Crystallographica Section A Foundations of Crystallography 64, a1 (August 23, 2008): C385. http://dx.doi.org/10.1107/s0108767308087692.

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48

Lowe, John A., Shari L. DeNinno, Susan E. Drozda, Christopher J. Schmidt, Karen M. Ward, F. David Tingley, Mark Sanner, Don Tunucci, and James Valentine. "An octahydro-cyclopenta[c]pyrrole series of inhibitors of the type 1 glycine transporter." Bioorganic & Medicinal Chemistry Letters 20, no. 3 (February 2010): 907–11. http://dx.doi.org/10.1016/j.bmcl.2009.12.071.

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49

Ryu, Chung-Kyu, Aram Kim, Hyun Ah Im, and Ji Young Kim. "Synthesis and antifungal activity of 1-thia-4b-aza-cyclopenta[b]fluorene-4,10-diones." Bioorganic & Medicinal Chemistry Letters 22, no. 18 (September 2012): 5777–79. http://dx.doi.org/10.1016/j.bmcl.2012.07.097.

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50

Schumann, Herbert, Klaudia Sühring, Roman Weimann, and Markus Hummert. "Deca(4-methylbenzyl)ferrocen und -stannocen / Deca(4-methylbenzyl)ferrocene and -stannocene." Zeitschrift für Naturforschung B 60, no. 5 (May 1, 2005): 527–32. http://dx.doi.org/10.1515/znb-2005-0508.

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Cyclopentadiene reacts with five equivalents of 4-methylbenzylalcohol (1:5,6 mole ratio) and sodium yielding penta(4-methylbenzyl)cyclopenta-2,4-diene (1), which upon treatment with butyl lithium affords the lithium salt [(4-MeC6H4CH2)5C5]Li (2). The reactions of 2 with FeCl2 and SnCl2 result in the formation of deca(4-methylbenzyl)ferrocene (3) and deca(4-methylbenzyl)stannocene (4), respectively. The 1H and 13C NMR, IR and mass spectra of the new compounds as well as the single crystal X-ray structure analysis of 1 are reported and discussed.

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