Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

• Sarot Cheenpracha,
• Ratchanaporn Chokchaisiri,
• Lucksagoon Ganranoo,
• Sareeya Bureekaew,
• Thunwadee Limtharakul and
• Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

• and 6β-cinnamoyl-7β-hydroxyvouacapen-5α-ol, have been reported to exhibit significant α-glucosidase inhibitory activity [5]. The genus Pterolobium, comprising approximately 10 species distributed widely in Africa, China, and Thailand [6], is flowering shrubs belonging to Fabaceae. There are only four

Sequential hydrozirconation/Pd-catalyzed cross coupling of acyl chlorides towards conjugated (2E,4E)-dienones

• Benedikt Kolb,
• Daniela Silva dos Santos,
• Sanja Krause,
• Anna Zens and
• Sabine Laschat

Beilstein J. Org. Chem. 2023, 19, 176–185, doi:10.3762/bjoc.19.17

• ). While the reaction with cinnamoyl chloride (26m) gave only 12% of desired dienone 27am (Table 4, entry 13), the yield increased up to 40% by using crotonoyl chloride 26o instead (Table 4, entry 15). In general, by using aliphatic acyl chlorides, the yields increased, e.g., nonanoyl chloride (26n

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

• Esteban P. Urriolabeitia,
• Pablo Sánchez,
• Alexandra Pop,
• Cristian Silvestru,
• Eduardo Laga,
• Ana I. Jiménez and
• Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

• (Figure 3), by reaction of N-cinnamoylglycine (1) with the corresponding benzaldehyde ArCHO in acetic anhydride as solvent and in the presence of sodium acetate [42][43][44][45][46][47][48]. In turn, N-cinnamoylglycine (1) was prepared following the Schotten–Baumann method from glycine and cinnamoyl

Practical tetrafluoroethylene fragment installation through a coupling reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide with various electrophiles

• Ken Tamamoto,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 2375–2383, doi:10.3762/bjoc.14.213

• temperature, significantly improved the yield of 6g. Acid chlorides with a heteroaromatic moiety, e.g., 5h and 5i, could also readily participate in the coupling reaction, leading to 6h and 6i in 83% and 87% isolated yields, respectively. Additionally, cinnamoyl chloride (5j) and n-octanoyl chloride (5k) were

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• acid units (e.g., β-methylaspartic acid and 2,3-diaminopropanoic acid) and a previously unreported 2-heptatrienyl cinnamoyl chain unit [107]. Dung beetle larvae are prone to bacterial and fungal infestations during their development inside the faeces balls. Although the direct involvement of defensive

Supramolecular structures based on regioisomers of cinnamyl-α-cyclodextrins – new media for capillary separation techniques

• Gabor Benkovics,
• Ondrej Hodek,
• Martina Havlikova,
• Zuzana Bosakova,
• Pavel Coufal,
• Milo Malanga,
• Eva Fenyvesi,
• Andras Darcsi,
• Szabolcs Beni and
• Jindrich Jindrich

Beilstein J. Org. Chem. 2016, 12, 97–109, doi:10.3762/bjoc.12.11

• of monocinnamyl-α-CDs, where the rigid double bond in the cinnamyl (Cin) moiety should prevent the self-inclusion of the phenyl ring to the CD cavity and prefer the formation of intermolecular complexes in polar solvents. The conjugation of the cinnamoyl (Cio) moiety with α- and β-CD through amide

• and ester linkages was already reported by Harada et al. [8][9]. These monosubstituted derivatives formed different types of supramolecular assemblies (dimers, cyclic oligomers, linear polymers) in water depending on the position of the cinnamoyl moiety on the CD rim. It was also experimentally proven

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

• Pablo Wessig,
• Roswitha Merkel and
• Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

• functionalizations in terminal positions. First applications were presented with pyrene, cinnamoyl and anthracenyl labelled ARs. Keywords: articulated rods; click chemistry; molecular rods; oligospiroketals; pyrene excimer; Introduction One of the basic principles in living nature is based on shape-persistent and

• [4 + 4] photocycloaddition of anthracene derivatives. At first we pursued a sequential approach by introducing the pyrene-1-ylacetyl and the cinnamoyl moieties in a two-step sequence in 4-hydroxypiperidine with subsequent oxidation to give piperidin-4-ones 27a,b. An appropriate anthracene derivative

• give 36 (Scheme 8). Besides the widely used CuAAC ligation the Staudinger ligation [22] is also an important tool for coupling molecules. To verify that the diazide 34 is also suitable for this reaction we first prepared the cinnamoyl substituted phosphane 38 from (2-hydroxyphenyl)diphenylphosphane (37

Unusual polymorphism in new bent-shaped liquid crystals based on biphenyl as a central molecular core

• Anna Kovářová,
• Svatopluk Světlík,
• Václav Kozmík,
• Jiří Svoboda,
• Vladimíra Novotná,
• Damian Pociecha,
• Ewa Gorecka and
• Natalia Podoliak

Beilstein J. Org. Chem. 2014, 10, 794–807, doi:10.3762/bjoc.10.75

• ], semifluorinated alkyl chains [14][20], and fullerene [21] into the terminal chain(s), variation of the linkage groups [10][22][23][24] (ester, azo, azoxy, imine, H-bond, cinnamoyl). Also dimeric, dendritic, and polymeric liquid crystals possessing the biphenyl moiety in the centre of the bent mesogenic unit were

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

• Andivelu Ilangovan and
• Shanmugasundar Saravanakumar

Beilstein J. Org. Chem. 2014, 10, 127–133, doi:10.3762/bjoc.10.9

• compound, no other literature precedence is available till now. Duong et al. have isolated three cinnamoyl bisamide derivatives, two new compounds grandiamide D, gigantamide A and the known compound dasyclamide (Figure 2) from the leaves of Aglaia gigantea [7]. Even though the structures were determined by

Exceptionally small supramolecular hydrogelators based on aromatic–aromatic interactions

• Junfeng Shi,
• Yuan Gao,
• Zhimou Yang and
• Bing Xu

Beilstein J. Org. Chem. 2011, 7, 167–172, doi:10.3762/bjoc.7.23

• /bjoc.7.23 Abstract We report herein the use of an aromatic–aromatic interaction to produce small molecule hydrogelators that self-assemble in water and form molecular nanofibers in the resulting hydrogels. Among these hydrogelators, a hydrogelator (6) made from a phenylalanine and a cinnamoyl group

• properties. Notably, compound 6 can undergo cis/trans-isomerization upon UV irradiation. Keywords: aromatic–aromatic interaction; cinnamoyl; hydrogel; hydrogelator; supramolecular; Introduction Gels formed by three-dimensional, elastic networks to encapsulate a liquid [1], have many useful properties (e.g

• , fluorenyl, naphthyl, naphthalenoxyl, and cinnamoyl groups, to covalently attach to the phenylalanine via a simple amide bond. On treatment with 1N NaOH solution, all the prepared compounds dissolve. However, when the pH of the solution is changed from basic to slightly acidic, compounds 1, 3, 4 and 6 form

Microwave- assisted ring closure reactions: Synthesis of 8-substituted xanthine derivatives and related pyrimido- and diazepinopurinediones

• Joachim C. Burbiel,
• Jörg Hockemeyer and
• Christa E. Müller

Beilstein J. Org. Chem. 2006, 2, No. 20, doi:10.1186/1860-5397-2-20

• reflux conditions had failed; no reaction was observed, even after several days. Heating of the uracil-cinnamoyl-amide 6 in HMDS in the presence of a catalytic amount of ammonium sulfate at 170°C in a sealed pressure tube yielded 93 % of the xanthine derivative 7 after a long reaction time of 9 h, as