5-溴海因 | 173904-10-4

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-溴海因
• 英文名称: 5-bromohydantoin
• 英文别名: 5-Bromoimidazolidine-2,4-dione
• CAS: 173904-10-4
• 化学式: C₃H₃BrN₂O₂
• 分子量: 178.973
• InChiKey: SAFCTMWBPBVFII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴海因 、 亚磷酸三乙酯 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以1.44 g的产率得到5-风化煤磷酸二乙酯
  参考文献：
  名称：

  5-亚甲基乙内酰脲的合成与反应性

  摘要：

  可以通过不同的合成途径获得5-亚甲基乙内酰脲，以及N-单-和N，N-二-保护的衍生物。这些化合物可以进行多种反应，例如不同类型亲核试剂的Diels–Alder反应，环氧化反应，甲醇加成反应和共轭加成反应，包括碳（氰化物），氮（哌啶）和硫（硫醇，硫代乙酸酯）亲核试剂。在酸性介质中，与亲电试剂（例如m- CPBA或甲醇）的反应性以及对路易斯酸促进共轭加成反应的需求表明乙内酰脲是一个较差的吸电子基团。

  DOI：

  10.1016/j.tet.2011.09.034
• 作为产物：
  描述：

  海因 在 溴 、 溶剂黄146 作用下， 反应 1.5h， 生成 5-溴海因
  参考文献：
  名称：

  合成对氨基鸟嘌呤B及其类似物

  摘要：

  通过乙内酰脲类化合物与α-溴代-间的关键偶联反应，完成了天然产物对位黄嘌呤B（2）及其类似物对位黄嘌呤C（3）和18-脱氧对位黄嘌呤B（4）的通用合成。苯乙酮衍生物。设计合成方法以解决制备更广泛的一组以Z-构型的5，6-双键为特征的对位黄嘌呤B类似物。

  DOI：

  10.1016/j.tet.2015.04.040

文献信息

• Azolidines as beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020032222A1

  公开（公告）日：2002-03-14

  This invention provides compounds of Formula I having the structure 1 wherein, A, X, Y, Z, W, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  本发明提供了具有以下结构式的I号化合物的药物或药用盐，其中A、X、Y、Z、W、R1、R2、R3、R4、R5和R6的定义如前所述。这些化合物可用于治疗或抑制与胰岛素抵抗或高血糖（通常与肥胖或葡萄糖不耐受有关）相关的代谢紊乱、动脉粥样硬化、胃肠疾病、神经源性炎症、青光眼、眼压增高和频繁排尿，特别是在治疗或抑制2型糖尿病方面特别有用。
• Process for preparing 5-arylhydantoins using 5-hydantoin, a halogenating
  申请人：Showa Denko K.K.

  公开号：US05606071A1

  公开（公告）日：1997-02-25

  The present invention provides a novel process for the preparation of 5-arylhydantoins as an important intermediate of (D)-arylglycines (e.g., (D)-p-hydroxyphenyl-glycine) useful for the synthesis of semisynthetic penicillines and cephalosporins, the process comprising (i) reacting a 5-unsubstituted hydantoin compound with a halogenating agent and (ii) reacting the resulting product with a p-unsubstituted phenol compound, the hydroxy group of which may be protected, to substitute the 5-position of the hydantoin compound with the phenol compound at the para position.

  本发明提供了一种新型的制备5-芳基咪唑啉的方法，作为(D)-芳基甘氨酸（例如(D)-对羟基苯甘氨酸）的重要中间体，用于合成半合成青霉素和头霉素，该方法包括(i)将5-未取代咪唑啉化合物与卤代试剂反应，(ii)将所得产物与p-未取代酚类化合物反应，其中酚类化合物的羟基可能被保护，以在咪唑啉化合物的5位与酚类化合物在对位进行取代。
• Identification of the hydantoin alkaloids parazoanthines as novel CXCR4 antagonists by computational and in vitro functional characterization
  作者：Rosa Maria Vitale、Stefano Thellung、Francesco Tinto、Agnese Solari、Monica Gatti、Genoveffa Nuzzo、Efstathia Ioannou、Vassilios Roussis、Maria Letizia Ciavatta、Emiliano Manzo、Tullio Florio、Pietro Amodeo

  DOI：10.1016/j.bioorg.2020.104337

  日期：2020.12

  CXCR4 chemokine receptor represents an attractive pharmacological target due to its key role in cancer metastasis and inflammatory diseases. Starting from our previously-developed pharmacophoric model, we applied a combined computational and experimental approach that led to the identification of the hydantoin alkaloids parazoanthines, isolated from the Mediterranean Sea anemone Parazoanthus axinellae, as novel CXCR4 antagonists. Parazoanthine analogues were then synthesized to evaluate the contribution of functional groups to the overall activity. Within the panel of synthesized natural and non-natural parazoanthines, parazoanthine-B was identified as the most potent CXCR4 antagonist with an IC₅₀ value of 9.3 nM, even though all the investigated compounds were able to antagonize in vitro the down-stream effects of CXC12, albeit with variable potency and efficacy. The results of our study strongly support this class of small molecules as potent CXCR4 antagonists in tumoral pathologies characterized by an overexpression of this receptor. Furthermore, their structure-activity relationships allowed the optimization of our pharmacophoric model, useful for large-scale in silico screening.
• Nakao, Kazuya; Asao, Masaaki; Shirai, Hiroki, Medicinal Chemistry Research, 1999, vol. 9, # 7-8, p. 631 - 642
  作者：Nakao, Kazuya、Asao, Masaaki、Shirai, Hiroki、Saito, Kiyoshi、Moriya, Tamon、Iwata, Hiroshi、Matsumoto, Mamoru、Matsuoka, Yuzo、Shimizu, Ryo

  DOI：——

  日期：——
• Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives
  作者：Nicholas A. Meanwell、Herbert R. Roth、Edward C. R. Smith、Donald L. Wedding、J. J. Kim Wright

  DOI：10.1021/jo00024a036

  日期：1991.11

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.