6372-02-7Relevant articles and documents
Total synthesis of the plasmoidal pigment physarorubinic acid, a polyenoyl tetramic acid
Dixon, Darren J.,Ley, Steven V.,Longbottom, Deborah A.
, p. 2231 - 2232 (1999)
The total synthesis of physarorubinic acid, a polyenoyltetramic acid plasmoidal pigment from Physarum polycephalum, is described in a series of steps from (E)-3-iodoacrylic acid 6 and employs aminolysis of the pentaene thioester 11 as a key synthetic step. Lacey-Dieckmann cyclisation and subsequent deprotection then affords physarorubinic acid 1 in high yield and purity.
Selective Ni-catalyzed cross-electrophile coupling of alkynes, fluoroalkyl halides, and vinyl halides
Chu, Lingling,Dai, Yubei,Wang, Fang,Zhu, Shengqing
supporting information, (2022/01/26)
We report a Ni-catalyzed three-component cross-electrophile coupling of alkynes with alkenyl halides and fluoroalkyl halides to generate fluoroalkyl-incorporated 1,3-dienes. This mild and operationally simple protocol is distinguished by its broad substra
Synthesis, radiolabeling, and preliminary in vivo evaluation of [68ga] ipcat-nota as an imaging agent for dopamine transporter
Farn, Shiou-Shiow,Chang, Kang-Wei,Lin, Wan-Chi,Yu, Hung-Man,Lin, Kun-Liang,Tseng, Yu-Chin,Chang, Yu,Yu, Chung-Shan,Lin, Wuu-Jyh
, p. 2577 - 2591 (2021/07/06)
Introduction: Novel radiotracer development for imaging dopamine transporters is a subject of interest because although [99mTc]TRODAT-1, [123I]β-CIT, and [123I]FP-CIT are commercially available;99Mo/99mTc generator is in short supply and123I production is highly dependent on compact cyclotron. Therefore, we designed a novel positron emission tomography (PET) tracer based on a tropane derivative through C-2 modification to conjugate NOTA for chelating68Ga, a radioisotope derived from a68Ge/68Ga generator. Methods: IPCAT-NOTA 22 was synthesized and labeled with [68Ga]GaCl4 ? at room tem-perature. Biological studies on serum stability, LogP, and in vitro autoradiography (binding assay and competitive assay) were performed. Furthermore, ex vivo autoradiography, biodis-tribution, and dynamic PET imaging studies were performed in Sprague Dawley rats. Results: [68Ga]IPCAT-NOTA 24 obtained had a radiochemical yield of ≥90% and a specific activity of 4.25 MBq/nmol. [68Ga]IPCAT-NOTA 24 of 85% radiochemical purity (RCP%) was stable at 37°C for up to 60 minutes in serum with a lipophilicity of 0.88. The specific binding ratio (SBR%) reached 15.8 ± 6.7 at 60 minutes, and the 85% specific uptake could be blocked through co-injection at 100-and 1000-fold of the cold precursor in in vitro binding studies. Tissue regional distribution studies in rats with [68Ga]IPCAT-NOTA 24 showed striatal uptake (0.02% at 5 minutes and 0.007% at 60 minutes) with SBR% of 6%, 25%, and 62% at 5–15, 30–40, and 60–70 minutes, respectively, in NanoPET studies. The RCP% of [68Ga]IPCAT-NOTA 24 at 30 minutes in vivo remained 67.65%. Conclusion: Data described here provide new information on the design of PET probe of conjugate/pendent approach for DAT imaging. Another chelator or another direct method of intracranial injection must be used to prove the relation between [68Ga]IPCAT-NOTA 24 uptake and transporter localization.
Using Nature's polyenes as templates: studies of synthetic xanthomonadin analogues and realising their potential as antioxidants
Madden, Katrina S.,Jokhoo, Hans R. E.,Conradi, Fabian D.,Knowles, Jonathan P.,Mullineaux, Conrad W.,Whiting, Andrew
supporting information, p. 3752 - 3759 (2019/04/17)
Two truncated analogues of the polyenyl photoprotective xanthomonadin pigments have been synthesised utilising an iterative Heck-Mizoroki (HM)/iododeboronation cross coupling approach and investigated as models of the natural product photoprotective agent
A low temperature, vinylboronate ester-mediated, iterative cross-coupling approach to xanthomonadin polyenyl pigment analogues
Madden, Katrina S.,Knowles, Jonathan P.,Whiting, Andrew
, (2019/10/19)
Approaches to the polyene natural product xanthomonadin, an octaenyl electron-deficient bacterial photoprotective agent, and its debromo analogue, were developed. These involved the iterative cross-coupling of multiple C2-fragments, using a vinylboronate
Palladium-catalyzed stereoretentive olefination of unactivated C(sp3)-H bonds with vinyl iodides at room temperature: Synthesis of β-vinyl α-amino acids
Wang, Bo,Lu, Chengxi,Zhang, Shu-Yu,He, Gang,Nack, William A.,Chen, Gong
supporting information, p. 6260 - 6263 (2015/02/19)
A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp3)-H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp3)-H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.
Structure-based optimization of click-based histone deacetylase inhibitors
Hou, Jingli,Feng, Congran,Li, Zhonghua,Fang, Qinghong,Wang, Huihui,Gu, Guoxian,Shi, Yikang,Liu, Pi,Xu, Feng,Yin, Zheng,Shen, Jie,Wang, Peng
scheme or table, p. 3190 - 3200 (2011/07/29)
Previously, we reported a click-chemistry based approach to the synthesis of a novel class of histone deacetylase (HDAC) inhibitors [1]. The lead compound NSC746457 was found to be as potent as SAHA (Vorinostat). Further optimization of NSC746457 by using
PREPARATION AND UTILITY OF SUBSTITUTED ALLYLAMINES
-
Page/Page column 61-62, (2008/12/06)
Disclosed herein are substituted allylamines having structural Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and the methods of their use thereof. (I)
Histone deacetylase inhibitors through click chemistry
Shen, Jie,Woodward, Robert,Kedenburg, James Patrick,Liu, Xianwei,Chen, Min,Fang, Lanyan,Sun, Duxin,Wang, Peng George
experimental part, p. 7417 - 7427 (2009/12/26)
Histone deacetylase inhibitors (HDACi) are a relatively new class of chemotherapy agents. Herein, we report a click-chemistry based approach to the synthesis of HDACi. Fourteen agents were synthesized from the combination of two alkyne and seven azido pre
Mechanistic studies on the Heck-Mizoroki cross-coupling reaction of a hindered vinylboronate ester as a key approach to developing a highly stereoselective synthesis of a C1-C7 Z,Z,E,-triene synthon for viridenomycin
Batsanov, Andrei S.,Knowles, Jonathan P.,Whiting, Andrew
, p. 2525 - 2532 (2008/02/02)
Mechanistic studies of the Heck-Mizoroki reaction of a vinylboronate ester with electronically different (four-substituted) aryl iodides shows that electron donors accelerate the cross-coupling, demonstrating that the oxidative addition step is not rate d
