2,4-dihydroxybenzoic acid N-hydroxysuccinimidyl ester | 186371-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-dihydroxybenzoic acid N-hydroxysuccinimidyl ester
• 英文别名: 2,5-Dioxo-1-pyrrolidinyl 2,4-Dihydroxybenzoate；(2,5-dioxopyrrolidin-1-yl) 2,4-dihydroxybenzoate
• CAS: 186371-01-7
• 化学式: C₁₁H₉NO₆
• 分子量: 251.196
• InChiKey: BYTXJVDUWGLIRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-dihydroxybenzoic acid N-hydroxysuccinimidyl ester 在 palladium on activated charcoal TEA 、 ammonium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 N-(3-aminopropyl-β-alanyl)-N'-(2,4-dihydroxybenzoyl-L-asparaginyl)-1,5-pentanediamine
  参考文献：
  名称：

  Syntheses and Biological Activities of Joro Spider Toxin Analogs to Spidamine and Joramine.

  摘要：

  为了研究在Joro蜘蛛（Nephila clavata）毒液中发现的spidamine和joramine的结构-活性关系，我们尝试合成各种类似物。根据我们之前合成spidamine的的方法，我们共合成了六种类似物，分别是N-(3-氨基丙基-β-丙氨酸)-N'-(2, 4-二羟基苯乙酰-L-天冬氨酰)-1, 5-戊二胺和joramine，N-(3-氨基丙基-β-丙氨酸)-N'-(4-羟基苯乙酰-L-天冬氨酰)-1, 5-戊二胺。这些类似物及四种中间体的生物活性与合成的spidamine和joramine在三种生物测定系统中进行了比较，包括龙虾神经肌肉突触、蟑螂和蚊子幼虫。在这些系统中，某些类似物抑制了谷氨酸受体，而含有D-天冬氨酸或吲哚乙酰的类似物被发现是强抑制剂。这些化合物在农药方面具有潜在应用前景。

  DOI：

  10.1248/cpb.45.93
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 2,4-二羟基苯甲酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 3.0h， 以55%的产率得到2,4-dihydroxybenzoic acid N-hydroxysuccinimidyl ester
  参考文献：
  名称：

  Syntheses and Biological Activities of Joro Spider Toxin Analogs to Spidamine and Joramine.

  摘要：

  为了研究在Joro蜘蛛（Nephila clavata）毒液中发现的spidamine和joramine的结构-活性关系，我们尝试合成各种类似物。根据我们之前合成spidamine的的方法，我们共合成了六种类似物，分别是N-(3-氨基丙基-β-丙氨酸)-N'-(2, 4-二羟基苯乙酰-L-天冬氨酰)-1, 5-戊二胺和joramine，N-(3-氨基丙基-β-丙氨酸)-N'-(4-羟基苯乙酰-L-天冬氨酰)-1, 5-戊二胺。这些类似物及四种中间体的生物活性与合成的spidamine和joramine在三种生物测定系统中进行了比较，包括龙虾神经肌肉突触、蟑螂和蚊子幼虫。在这些系统中，某些类似物抑制了谷氨酸受体，而含有D-天冬氨酸或吲哚乙酰的类似物被发现是强抑制剂。这些化合物在农药方面具有潜在应用前景。

  DOI：

  10.1248/cpb.45.93

文献信息

• New Bitter-Masking Compounds:  Hydroxylated Benzoic Acid Amides of Aromatic Amines as Structural Analogues of Homoeriodictyol
  作者：Jakob P. Ley、Maria Blings、Susanne Paetz、Gerhard E. Krammer、Heinz-Jürgen Bertram

  DOI：10.1021/jf0617061

  日期：2006.11.1

  hydroxybenzoic acid amides of benzylamines were synthesized and evaluated as masking agents toward bitterness of caffeine by sensory methods. The closest structural relatives of homoeriodictyol, the hydroxybenzoic acid vanillylamides 5-9, were the most active and were able to reduce the bitterness of a 500 mg L(-1) caffeine solution by about 30% at a concentration of 100 mg L(-1). 2,4-Dihydroxybenzoic acid vanillylamide

  从已知的来自苦艾草的苦味掩盖黄烷酮香茅醇和高香茅醇开始，合成了一些结构上相关的苄基胺的羟基苯甲酰胺，并通过感官方法评价了其作为咖啡因苦味的掩盖剂。最高间苯三酚的结构亲戚，羟基苯甲酸vanillylamides 5-9，是最活跃的，能够在浓度为100 mg L（-）的情况下将500 mg L（-1）咖啡因溶液的苦味降低约30％。 1）。2,4-二羟基苯甲酸香草酰胺7表现出明显的剂量依赖性活性，可抑制5至500 mg L（-1）中的咖啡因苦味。另外，可以减少奎宁和水杨酸的苦味，但不能减少苦肽N1-亮氨酰-1-色氨酸的苦味。高雌三醇和酰胺7的组合显示没有协同或拮抗活性的变化。模型化合物7的结果表明，迄今未知的黄烷酮和新酰胺的掩盖机理可能相同。将来，新的酰胺可能会替代昂贵的黄烷酮，以创造掩盖药品或食品苦味的调味剂溶液。
• 3D-QSAR study of adamantyl N-benzylbenzamides as melanogenesis inhibitors
  作者：Yong Deog Hong、Heung Soo Baek、Haelim Cho、Soo Mi Ahn、Ho Sik Rho、Young-Ho Park、Yung Hyup Joo、Song Seok Shin

  DOI：10.1016/j.bmcl.2013.11.056

  日期：2014.1

  Three-dimensional quantitative structure-activity relationship (3D-QSAR) modeling, comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety were performed to understand the mechanism of action and structure-activity relationship of these compounds. Contour map analysis indicated that steric contributions of the adamantyl moiety and electrostatic contributions of the hydroxyl group at the 3-position are important in the activity. Activities of the training set and test sets predicted by CoMFA fit well with actual activities, demonstrating that CoMFA, along with the best calculated q(2) value, has the best predictive ability. (C) 2013 Elsevier Ltd. All rights reserved.
• Adamantyl N-benzylbenzamide: New series of depigmentation agents with tyrosinase inhibitory activity
  作者：Heung Soo Baek、Yong Deog Hong、Chang Seok Lee、Ho Sik Rho、Song Seok Shin、Young-Ho Park、Yung Hyup Joo

  DOI：10.1016/j.bmcl.2011.12.144

  日期：2012.3

  A new series of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety has been synthesized, and the depigmenting and tyrosinase inhibitory activities of the molecules were evaluated. The lipophilic character of the adamantyl moiety appeared to confer greater depigmentation power on the benzamide derivatives as compared to those lacking adamantyl substitution. Molecular modeling was applied in order to elucidate the interactions between ligands and tyrosinase that led to inhibition. (C) 2012 Elsevier Ltd. All rights reserved.
• Syntheses and Biological Activities of Joro Spider Toxin Analogs to Spidamine and Joramine.
  作者：Tadashige CHIBA、Toshifumi AKIZAWA、Motomi MATSUKAWA、Nobufumi KAWAI、Yoshiaki KONO、Masanori YOSHIOKA

  DOI：10.1248/cpb.45.93

  日期：——

  In order to study the structure-activity relationships of spidamine and joramine found in the venom of Joro spider, Nephila clavata, we attempted to synthesize various analogs. Six analogs were convergently synthesized according to our previous method for the synthesis of spidamine, N-(3-aminopropyl-β-alanyl)-N'-(2, 4-dihydroxy-phenylacetyl-L-asparaginyl)-1, 5-pentanediamine and joramine, N-(3-aminopropyl-β-alanyl)-N'-(4-hydroxyphenyl-acetyl-L-asparaginyl)-1, 5-pentanediamine. The biological activities of the analogs and four intermediates were compared with those of synthetic spidamine and joramine in three bioassay systems, lobster neuromuscular synapse, cockroaches and mosquito larvae. The glutamate receptors in these systems were inhibited by some analogs, and the D-asparagine- or indoleacetyl-containing analogs were found to be strong inhibitors. These compounds have potential application as insecticides.

  为了研究在Joro蜘蛛（Nephila clavata）毒液中发现的spidamine和joramine的结构-活性关系，我们尝试合成各种类似物。根据我们之前合成spidamine的的方法，我们共合成了六种类似物，分别是N-(3-氨基丙基-β-丙氨酸)-N'-(2, 4-二羟基苯乙酰-L-天冬氨酰)-1, 5-戊二胺和joramine，N-(3-氨基丙基-β-丙氨酸)-N'-(4-羟基苯乙酰-L-天冬氨酰)-1, 5-戊二胺。这些类似物及四种中间体的生物活性与合成的spidamine和joramine在三种生物测定系统中进行了比较，包括龙虾神经肌肉突触、蟑螂和蚊子幼虫。在这些系统中，某些类似物抑制了谷氨酸受体，而含有D-天冬氨酸或吲哚乙酰的类似物被发现是强抑制剂。这些化合物在农药方面具有潜在应用前景。