- Preparation method of 7-phenyl-6-heptynoic acid
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The invention relates to the field of organic chemistry, in particular to a preparation method of 7-phenyl-6-heptynoic acid. The invention provides a preparation method of 7-phenyl-6-heptynoic acid. The preparation method comprises the following steps: carrying out an alkylation reaction on phenyl acetylene and 5-halogenated valeronitrile in the presence of alkali to prepare a compound shown as aformula I; and hydrolyzing the compound shown as the formula I to prepare 7-phenyl-6-heptynoic acid. The provided preparation method of 7-phenyl-6-heptynoic acid has the advantages that raw materialsand auxiliary materials are cheap and easily available, the cost is low; the reaction conditions are mild, the reaction steps are few, the reaction is stable and controllable, especially the cyano hydrolysis reaction and active sites are few, the side reaction happens difficultly, the product can be obtained by adjusting the pH after the reaction is finished, the post-treatment is very simple andconvenient, the yield and quality of the whole route are good, the energy is saved, and the preparation method is environment-friendly.
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Paragraph 0044-0090
(2020/11/26)
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- Continuous flow method for synthesizing 3 - methyl -4 -butyryl -5 - nitrobenzoate and reaction device thereof (by machine translation)
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The invention discloses a continuous flow method for synthesizing 3 - methyl -4 - butyryl -5 - nitrobenzoate as a raw material, and the reaction device is prepared from 3 - methyl -4 - butyryl benzoic acid methyl ester as a raw material and mixed acid (nitric acid and sulfuric acid) as a nitration reagent and then continuously inputting the high-efficiency mixing device into a pipeline reactor for continuous liquid separation to obtain a pure product 3 - methyl -4 - butyryl -5 - nitrobenzoate. The continuous stream nitration reaction mixed acid is small in acid consumption, short in reaction time, high in conversion rate, less in byproduct and less in solid waste, accords with a green chemical concept. (by machine translation)
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Paragraph 0043-0090
(2020/11/26)
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- Design, Synthesis, and Biological Evaluation of 6-Benzoxazole Benzimidazole Derivatives with Antihypertension Activities
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A series of new angiotensin II receptor 1 antagonists were prepared. They displayed nanomolar affinity to AT1 receptor and could decrease blood pressure efficiently in spontaneously hypertensive rats. Among them, compounds 1b and 2b could reduce the blood pressure with more or equal potency compared to Losartan. So, compounds 1b and 2b could be considered as potential antihypertension drug candidates.
- Wu, Zhuo,Bao, Xiao-Lu,Zhu, Wei-Bo,Wang, Yan-Hui,Phuong Anh, Nguyen Thi,Wu, Xiao-Feng,Yan, Yi-Jia,Chen, Zhi-Long
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- N-Phenyl indole derivatives as AT1 antagonists with anti-hypertension activities: Design, synthesis and biological evaluation
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The design, synthesis, in vitro and in vivo evaluation of 6-substituted benzimidazole with 1, 4-disubsituted or 1, 5-disubsituted indole derivatives as novel angiotensin II receptor antagonists are outlined. Radioligand binding assays showed that several 6-substituted benzimidazole derivatives displayed high affinities binding to the angiotensin II type 1 receptor at the same order of magnitude to telmisartan. The biological evaluation on spontaneously hypertensive rats showed that 2-[4-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole-1-yl]methyl]-1H-indol-1-yl]benzoic acid, 1c, could cause significant decrease on MBP in a dose dependent manner. Its maximal response lowered 53 mmHg of MBP at 5 mg/kg and 64 mmHg of MBP at 10 mg/kg after oral administration, and the significant antihypertensive effect lasted beyond 24 h, which was better than both losartan and telmisartan. A study designed to determine acute toxicity showed that 1c had low acute toxicity with no significant changes in the weight and no obvious untoward reactions. The encouraging results make 1c an effective and durable anti-hypertension drug candidate and deserve further investigation for therapeutic application.
- Zhu, Weibo,Bao, Xiaolu,Ren, He,Da, Yajing,Wu, Dan,Li, Fuming,Yan, Yijia,Wang, Li,Chen, Zhilong
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p. 161 - 178
(2016/04/05)
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- METHOD FOR NITRATING ANILINE DERIVATIVES
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The present invention relates to a process for the highly regioselective aromatic nitration of alkyl 4-alkanoylamino-3-alkyl-benzoates in the 5-position in a mixture containing nitric acid and the use of the resulting products for preparing, in particular, pharmaceutically active benzimidazole derivatives.
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Page/Page column 5
(2008/06/13)
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- Facile Synthesis of Novel Nonpeptide Angiotensin II Receptor Antagonists
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A series of Losartan analogues 1-12 with different functional groups were synthesized and characterized. In comparison with the previous reports, the synthetic procedures described in this paper have been optimized as follows below: 1) preparation of aromatic amine 15 and 18 through hydrogenation by employing Raney Ni and hydrazine as catalysts in place of palladium; 2) preparation of nitro-compound 17 by using pure fuming nitric acid at -20 - -15°C; 3) alkylation of 21 with 22 or 23 in the presence of sodium hydride in place of potassium tert-butylate; 4) preparation of carboxylic acid 4 by ester cleavage rather than hydrolysis of cyano group.
- Yang, Ling-Chun,Qi, Chuan-Min,Zhang, Guan-Xin,Zou, Nan-Zhi
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p. 1107 - 1112
(2007/10/03)
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- 6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: Synthesis, biological activity, and structure-activity relationships
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Starting from the recently reported nonpeptidic angiotensin II (AII) receptor antagonists DuP 753 (1) and Exp 7711 (2), we have designed and investigated novel substituted benzimidazoles. Systematic variation of several substituents at the benzimidazole ring positions 4-7 led to the finding that substitution in position 6 with acylamino groups results in highly active AII antagonists. Compounds with 6-membered lactam or sultam substituents in position 6 of benzimidazole showed receptor activities in the low nanomolar range but were only weakly active when given orally to rats. In contrast, analogous substitution of the benzimidazole moiety with basic heterocycles resulted in potent AII antagonists which were also well absorbed after oral application. The most active compound of this series, 33 (BIBR 277), was selected as a candidate for clinical development. On the basis of molecular modeling studies a binding model of this new class of AII antagonists to the AT1 receptor is proposed.
- Ries,Mihm,Narr,Hasselbach,Wittneben,Entzeroth,Van Meel,Wienen,Hauel
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p. 4040 - 4051
(2007/10/02)
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