N-[(2-硝基苯基)磺酰基]-beta-丙氨酸 | 90558-39-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-[(2-硝基苯基)磺酰基]-beta-丙氨酸
• 英文名称: N-[(o-nitrophenyl)sulfonyl]-β-alanine
• 英文别名: 3-(2-nitrophenylsulfonamido)propanoic acid；3-(2-nitrobenzenesulfonamide)-1-propionic acid；3-Ns-aminopropionic acid；2-Nitro-benzolsulfonsaeure-<2-carboxy-aethylamid>；3-(2-nitrobenzenesulfonylamino)propionic acid；3-(2-Nitro-benzenesulfonylamino)-propionic acid；3-[(2-nitrophenyl)sulfonylamino]propanoic acid
• CAS: 90558-39-7
• 化学式: C₉H₁₀N₂O₆S
• mdl: MFCD00436346
• 分子量: 274.254
• InChiKey: GITSWRINOGOGRB-UHFFFAOYSA-N

物化性质

• 熔点：
  129.5-131 °C
• 沸点：
  523.7±60.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(2-硝基苯基)磺酰基]-beta-丙氨酸 在 potassium carbonate 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.25h， 生成 N-(3-(allyloxy)-3-oxopropyl)-N-(2-nitrobenzenesulfonyl)glycine
  参考文献：
  名称：

  N-取代的N-芳基磺酰基甘氨酸的制备及其在类肽合成中的应用

  摘要：

  为了增加类肽和肽-类肽杂化物可利用的化学多样性，N-烷基化的芳基磺酰胺被用于制备与固相合成兼容的侧链保护的N-取代的甘氨酸。所描述的方法可以通过四个简单的步骤从市售胺中获得带有多种官能团的类肽单体。制备的N-取代的N-芳基磺酰基甘氨酸在固相合成中用作单体，以将相关的官能化侧链引入类肽低聚物和肽-类肽杂化物中。

  DOI：

  10.1021/acs.orglett.5b02862
• 作为产物：
  描述：

  3-氨基丙酸甲酯盐酸盐 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 N-[(2-硝基苯基)磺酰基]-beta-丙氨酸
  参考文献：
  名称：

  PYRAZOLE DERIVATIVES, MEDICINAL COMPOSITION CONTAINING THE SAME, MEDICINAL USE THEREOF, AND INTERMEDIATE FOR PRODUCTION THEREOF

  摘要：

  公开号：

  EP1548024B1

文献信息

• Synthesis of oxidative metabolites of K-115, a novel Rho-kinase inhibitor
  作者：Noriaki Gomi、Kimiyuki Shibuya、Kiyoshi Kawamura、Mototsugu Kabeya

  DOI：10.1016/j.tetlet.2021.153589

  日期：2022.2

  / 3A5 in human liver S9 and hepatocytes. We synthesized the proposed compounds 2–4 and determined the metabolite structure by LC-MS/MS analysis. Metabolites 2–4 were synthesized by rearrangement of isoquinoline N-oxide and/or by using (S)-5-keto-2-methyl-1,4-diazepane moiety as a key structure, which in turn was prepared from (R)-3-amino-2-propanol and 3-amino-propionic acid through a Mitsunobu intramolecular

  在人体中， ( S )-4-fluoro-5-(2-methyl-1,4-diazepan-1-ylsulfonyl)-isoquinoline hydrochloride dihydrate (K-115, 1 ) 的氧化代谢物2 – 4，一种新型 Rho-激酶抑制剂，主要由人肝脏 S9 和肝细胞中的醛氧化酶和 CYP3A4 / 3A5 形成。我们合成了建议的化合物2-4，并通过 LC- MS /MS 分析确定了代谢物结构。代谢物2-4是通过异喹啉N-氧化物的重排和/或使用 ( S )-5-keto-2-methyl - 1,4 -diazepane 部分作为关键结构合成的，而后者又由 ( R)-3-氨基-2-丙醇和3-氨基-丙酸通过Mitsunobu分子内环化反应。
• TRAM Linker:  A Safety-Catch Linker for the Traceless Release of Acrylamides
  作者：Christopher J. Ciolli、Sean Kalagher、Peter J. Belshaw

  DOI：10.1021/ol049711i

  日期：2004.6.1

  [reaction: see text] A novel safety-catch linker for the solid-phase synthesis of small-molecule libraries containing electrophilic reactive groups has been developed. Upon cleavage from solid support, the linker generates a Michael acceptor (an acrylamide) on each library member. Utilization of a two-resin system in the final cleavage step provides crude products in high purity, allowing direct use

  [反应：见正文]已开发出一种新型的安全捕捉连接器，用于固相合成包含亲电反应基团的小分子文库。从固体支持物上裂解后，连接子在每个文库成员上生成一个迈克尔受体（丙烯酰胺）。在最终裂解步骤中使用双树脂系统可提供高纯度的粗产物，可在过滤和蒸发后直接用于生物测定。
• Pyrazole derivatives, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof
  申请人：Fushimi Nobuhiko

  公开号：US20050272669A1

  公开（公告）日：2005-12-08

  The present invention provides pyrazole derivatives represented by the general formula: wherein R 1 represents H, an optionally substituted C 1-6 alkyl group etc.; one of Q and T represents a group represented by the general formula: or a group represented by the general formula: while the other represents an optionally substituted C 1-6 alkyl group etc.; R 2 represents H, a halogen atom, OH, an optionally substituted C 1-6 alkyl group etc.; X represents a single bond, O or S; Y represents an optionally substituted C 1-6 alkylene group etc.; Z represents —R B , —COR C etc. in which R B represents an optionally substituted C 1-6 alkyl group etc.; and R C represents an optionally substituted C 1-6 alkyl group etc.; R 4 represents H, an optionally substituted C 1-6 alkyl group etc.; and R 3 , R 5 and R 6 represent H, a halogen atom etc., pharmaceutically acceptable salts thereof or prodrugs thereof, which exhibit an excellent inhibitory activity in human SGLT1 and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, impaired glucose tolerance, impaired fasting glycemia, diabetic complications or obesity, and a disease associated with the increase of blood galactose level such as galactosemia, and pharmaceutical compositions comprising the same, pharmaceutical uses thereof, and intermediates for production thereof.

  本发明提供了由通式表示的吡唑衍生物：其中，R1代表H、可选取代的C1-6烷基等；Q和T中的一个代表由通式表示的基团：或由通式表示的基团：另一个代表可选取代的C1-6烷基等；R2代表H、卤素原子、OH、可选取代的C1-6烷基等；X代表单键、O或S；Y代表可选取代的C1-6亚烷基等；Z代表-RB、-CORC等，其中RB代表可选取代的C1-6烷基等；RC代表可选取代的C1-6烷基等；R4代表H、可选取代的C1-6烷基等；R3、R5和R6代表H、卤素原子等，其药学上可接受的盐或前药，具有在人类SGLT1中出色的抑制活性，可用作预防或治疗与高血糖相关的疾病，如糖尿病、糖耐量受损、空腹血糖受损、糖尿病并发症或肥胖症，以及与血中半乳糖水平增加相关的疾病，如半乳糖血症的治疗剂，以及包含它们的制药组合物、制药用途和制备它们的中间体。
• General Synthesis of β-Alanine-Containing Spider Polyamine Toxins and Discovery of <i>Nephila</i> Polyamine Toxins 1 and 8 as Highly Potent Inhibitors of Ionotropic Glutamate Receptors
  作者：Simon Lucas、Mette H. Poulsen、Niels G. Nørager、Anne F. Barslund、Tinna B. Bach、Anders S. Kristensen、Kristian Strømgaard

  DOI：10.1021/jm301255m

  日期：2012.11.26

  Certain spiders contain large pools of polyamine toxins, which are putative pharmacological fools awaiting further discovery. Here we present a general synthesis strategy for this class of-toxins and prepare five structurally varied polyamine toxins. Electrophysiological testing at three ionotropic glutamate receptor subtypes reveals that two of these, Nephila polyamine toxins 1 (NPTX-1) and 8 (NPTX-8), comprise intriguing pharmacological activities by having subnanomolar IC50 values at kainate receptors.
• Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution:  Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-ones and of Their Benzo-Fused Derivatives
  作者：Luca Banfi、Andrea Basso、Giuseppe Guanti、Nicola Kielland、Claudio Repetto、Renata Riva

  DOI：10.1021/jo062626z

  日期：2007.3.1

  A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.