Preparation of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetamide derivatives as novel arginine vasopressin V2 receptor agonists

Tsukamoto, Issei; Koshio, Hiroyuki; Akamatsu, Seijiro; Kuramochi, Takahiro; Saitoh, Chikashi; Yatsu, Takeyuki; Yanai-Inamura, Hiroko; Kitada, Chika; Yamamoto, Eisaku; Sakamoto, Shuichi; Tsukamoto, Shin‐ichi

doi:10.1016/j.bmc.2008.09.039

Cited by 11 publications

(8 citation statements)

References 10 publications

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“…转而考察在硫酸存在下将氰基水解为酸的方法 [26] , 遗憾的是反应仅停留在中间体 4 的步骤. 有文献报道, 酰胺可以在 NaNO 2 /H 2 SO 4 的存在下平稳地水解为羧酸 [27] , 于是采取两步法来实现氰基向羧酸的转化, 取得了进展. 首先中间体 3 在浓度为 80%的硫酸水溶液中在 100 ℃反应 10 h, 实现了氰基向酰胺的完全转化得到中间体 4.…”

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Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Jiang¹,

Cheng²,

Shen³

et al. 2020

Chin. J. Org. Chem.

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The synthetic route of substituted 1,2,4-triazole benzamide derivatives was explored, which included several steps such as catalytic cross-coupling of 2,6-dichlorobenzonitrile with a triazole, amidation of nitrile, diazotization of amide and hydrolysis, and amidation of acid. Unreported 14 new 1,2,4-triazole benzamide derivatives were synthesized. Their chemical structures were characterized by 1 H NMR, 13 C NMR and HRMS. Their antifungal activities against Gaeumannomyces graminis var. tritici and Fusarium pseudocerealum were evaluated in vitro by the plate method. The results indicated that antifungal activities of compound 2-chloro-N-phenyl-6-(1H-1,2,4-triazol-1-yl)benzamide (7i) against Gaeumannomyces graminis var. tritici reached up to 80% at the concentrations of 100 mg/L, and were comparable to the control level of silthiopham at the concentrations of 50 and 25 mg/L. However, these compounds didn't show obvious antifungal activities against Fusarium pseudocerealum. Keywords 1,2,4-triazobenzamide derivatives; synthesis; Gaeumannomyces graminis var. tritici; antifungal activity 芳甲酰胺类衍生物是具有广泛生物活性的一类化合物, 多年来备受关注. 苯甲酰衍生物在医药领域发挥着重要的作用, 取代的苯甲酰胺在精神分裂症抑制 [1] 、癌细胞的控制 [2][3] 、对感染 HIV-1 潜伏期细胞的清除 [4] 等方面发挥良好活性. 一些结构的苯甲酰胺作为鱼尼丁受体(RyR)抑制剂具有优良的杀虫活性 [5][6][7][8] , 已经商品化的有氯虫苯甲酰胺(Chlorantraniliprole) [9] 、溴氰虫酰胺 (Cyantraniliprole) [10] 等(图 1). 在除草剂领域, 苯甲酰胺衍生物可以抑制乙酰乳酸合成酶(AHAS), 从而发挥除草活性 [11] . 近年来, 芳甲酰胺类衍生物在杀菌剂领域的研究也比较活跃, 一系列的芳甲酰胺化合物被开发为杀菌剂 [12] , 如商品化的品种有啶酰菌胺(Boscalid)

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Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Jiang¹,

Cheng²,

Shen³

et al. 2020

Chin. J. Org. Chem.

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“…2). 8 As we reported previously, the chemical structure of the 'tail'-moiety (Fig. 2) in our compound strictly regulates agonist-antagonist switching for the vasopressin V 2 receptor.…”

Section: Introductionmentioning

confidence: 75%

“…Carboxylic acid (1q), which is the common intermediate for preparation of various amide derivatives, was synthesized from 2 in the same manner as reported in the previous paper. 8 Condensation of 1q with amines in the presence of N-ethyl-N 0 -(3-dimethylaminopropyl)carbodiimide hydrochloride (WSCD) and 1-hydroxybenzotriazole (HOBt) yielded the target compounds (1a-1p, 1s-1u, and 1w;Scheme 1). The carboxamide form (1r) was prepared from 1q and aqueous ammonia via activation by thionyl chloride (Scheme 2).…”

Section: Chemistrymentioning

confidence: 99%

“…2) in our compound strictly regulates agonist-antagonist switching for the vasopressin V 2 receptor. 8 In this paper, we describe the synthesis, biological activity, and structure-activity relationships (SARs) of the 'head'-moiety of 1a as investigated by replacing the 2-pyridilmethyl group with various other chemical groups. In addition to the binding affinities for the V 2 and V 1a receptors, the cAMP accumulation activity, in vivo action, and CYP inhibitory activity of some representative compounds are also shown.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and structure–activity relationships of amide derivatives of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetic acid as selective arginine vasopressin V2 receptor agonists

Tsukamoto

Koshio

Kuramochi

et al. 2009

Bioorganic & Medicinal Chemistry

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“…They all share a high primary sequence homology, but have great diversity in their functional properties ( Figure 3 ) [ 47 ]. V1a is a vascular receptor found primarily in vascular smooth muscle cells but was also discovered in platelets, liver, blood vessels, renal mesangial cells, brain, uterus and adrenal cortex [ 48 , 49 , 50 , 51 ]. Activated V1a receptor controls blood pressure, glycogenolysis and contraction of mesangial cells.…”

Section: Vasopressinmentioning

confidence: 99%

Vasopressin and Its Analogues: From Natural Hormones to Multitasking Peptides

Glavaš

Gitlin-Domagalska

Dębowski

et al. 2022

IJMS

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Human neurohormone vasopressin (AVP) is synthesized in overlapping regions in the hypothalamus. It is mainly known for its vasoconstricting abilities, and it is responsible for the regulation of plasma osmolality by maintaining fluid homeostasis. Over years, many attempts have been made to modify this hormone and find AVP analogues with different pharmacological profiles that could overcome its limitations. Non-peptide AVP analogues with low molecular weight presented good affinity to AVP receptors. Natural peptide counterparts, found in animals, are successfully applied as therapeutics; for instance, lypressin used in treatment of diabetes insipidus. Synthetic peptide analogues compensate for the shortcomings of AVP. Desmopressin is more resistant to proteolysis and presents mainly antidiuretic effects, while terlipressin is a long-acting AVP analogue and a drug recommended in the treatment of varicose bleeding in patients with liver cirrhosis. Recently published results on diverse applications of AVP analogues in medicinal practice, including potential lypressin, terlipressin and ornipressin in the treatment of SARS-CoV-2, are discussed.

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Preparation of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetamide derivatives as novel arginine vasopressin V2 receptor agonists

Cited by 11 publications

References 10 publications

Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Synthesis and structure–activity relationships of amide derivatives of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetic acid as selective arginine vasopressin V2 receptor agonists

Vasopressin and Its Analogues: From Natural Hormones to Multitasking Peptides

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