methyl ((2-nitrophenyl)sulfonyl)glycinate | 215056-52-3

• 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
• 英文名称: methyl ((2-nitrophenyl)sulfonyl)glycinate
• 英文别名: Methyl 2-(2-nitrobenzenesulfonamido)acetate；methyl 2-[(2-nitrophenyl)sulfonylamino]acetate
• CAS: 215056-52-3
• 化学式: C₉H₁₀N₂O₆S
• mdl: MFCD01213812
• 分子量: 274.254
• InChiKey: LDMGQCBNJVSAQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  107 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  445.6±55.0 °C(Predicted)
• 密度：
  1.455±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl ((2-nitrophenyl)sulfonyl)glycinate 在 sodium hydride 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-(1,1-dioxo-4,5-dihydro-3H-1lambda6,2,5-benzothiadiazepin-2-yl)acetate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Benzothiadiazepine Hydroxamates as Selective Tumor Necrosis Factor-α Converting Enzyme Inhibitors

  摘要：

  Elevated levels of tumor necrosis factor-alpha (TNF-alpha) have been associated with several inflammatory diseases, and therefore, strategies for its suppression have become important targets in drug discovery. Our efforts to suppress TNF-alpha have centered on the inhibition of TNF-alpha converting enzyme (TACE) through the use of hydroxamate inhibitors. Starting from broad-spectrum matrix metalloproteinase (MMP) inhibitors, we have designed and synthesized novel benzothiadiazepines as potent and selective TACE inhibitors. The benzothiadiazepines were synthesized with variation in P1 and P1' in order to effect potency and selectivity. The inhibitors were evaluated versus porcine TACE (pTACE), and the initial selectivity was assessed with counterscreens of MMP-1, -2, and -9. Several potent and selective inhibitors were discovered with compound 41 being the most active against pTACE (K-i = 5 nM) while still maintaining good selectivity versus the MMP's (at least 75-fold). Most compounds were assessed in the human peripheral blood mononuclear cell assay (PBMC) and the human whole blood assay (WBA) to determine their ability to suppress TNF-alpha. Compound 32 was the most potent compound in the PBMC assay (IC50 = 0.35 muM), while compound 62 was the most active in the WBA (IC50 = 1.4 muM).

  DOI：

  10.1021/jm020475w
• 作为产物：
  描述：

  邻硝基苯磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 methyl ((2-nitrophenyl)sulfonyl)glycinate
  参考文献：
  名称：

  通过 Oxyma-O-磺酸盐合成磺酰胺 - 与酸敏感基团和固相肽合成的兼容性

  摘要：

  报道了一种通过将磺酸基活化为相应的 2-氰基-2-(羟基亚氨基)乙酸乙酯 (Oxyma) 磺酸酯来合成磺胺类药物的更温和、更有效的方法。为此，此方法比所有其他现有协议更环保。其他重要优势在于 (a) 在环境和温和条件下适用于亲核性较低的苯胺，以及 (b) 与固相肽合成和酸不稳定基团如三苯甲基 (Trt) 和 tBu 的相容性，这使固相合成成为可能各种肽的磺胺类药物。为了说明这一点，使用基于 Fmoc 的固相肽合成 (SPPS) 证明了肽 GAILG-NH2 的三种磺酰胺衍生物的合成，这与治疗 2 型糖尿病的药物设计相关。

  DOI：

  10.1002/ejoc.201201571

文献信息

• Piperazine derivative
  申请人：Kowa Co., Ltd.

  公开号：US06432957B1

  公开（公告）日：2002-08-13

  A piperazine compound represented by formula (1): wherein X is —CH2—, —C(O)— or —CH(CH3)—; R1 is a hydrogen atom or alkyl group; and R2 is a hydrogen atom, alkyl group, hydroxyalkyl group, arylalkyl group, heteroarylalkyl group, carboxyalkyl group, carboxamidoalkyl group, aminoalkyl group or guanidinoalkyl group; an acid-addition salt thereof, or a hydrate thereof. The compound has excellent inhibitory effects on both cell adhesion and cell infiltration and is useful for prevention or treatment of diseases such as allergy, asthma, rheumatism, arteriosclerosis and inflammation.

  一种由化学式（1）表示的哌嗪化合物： 其中X为—CH2—、—C(O)—或—CH(CH3)—；R1为氢原子或烷基基团；R2为氢原子、烷基基团、羟基烷基基团、芳基烷基基团、杂环芳基烷基基团、羧基烷基基团、羧胺基烷基基团、氨基烷基基团或胍基烷基基团；其酸加合盐，或其水合物。该化合物对细胞粘附和细胞浸润均具有出色的抑制作用，并可用于预防或治疗过敏、哮喘、风湿病、动脉硬化和炎症等疾病。
• Trimodular Solution‐Phase Protocol for Rapid Large‐Scale Synthesis of Hydrogen Bond Surrogate‐Constrained α‐Helicomimics
  作者：Sunit Pal、Erode N. Prabhakaran

  DOI：10.1002/ejoc.202001359

  日期：2021.3.19

  cost‐effective, high‐yielding, rapid trimodular solution‐phase method has been demonstrated to synthesize the hydrogen bond surrogate (HBS) constrained single α‐helical turn and C‐terminal extended helices. The HBS‐constrained α‐helicomimic is divided into three modules and each of them was synthesized in 100 mmol scale followed by connecting them to adopt the α‐helicomimic.

  已经证明了一种经济高效，高产量的快速三模溶液相方法可以合成氢键替代物（HBS）约束的单个α螺旋圈和C端扩展螺旋。将受HBS约束的α螺旋体分为三个模块，每个模块以100 mmol的比例合成，然后将它们连接起来以采用α螺旋体。
• Methyl 2-(Bromomethyl)acrylate, Methyl Acrylate, and Glycine in the Synthesis of Functionalized Pyrrolidones
  作者：N. K. Selezneva、Z. R. Valiullina、A. M. Galeeva、L. V. Spirikhin、M. S. Miftakhov

  DOI：10.1134/s1070428018110076

  日期：2018.11

  Possible application of methyl 2-(bromomethyl)acrylate, methyl acrylate, and glycine in the synthesis of functionalized pyrrolidones was considered.

  考虑了2-（溴甲基）丙烯酸甲酯，丙烯酸甲酯和甘氨酸在官能化吡咯烷酮合成中的可能应用。
• Conformational modulation of peptides using β-amino benzenesulfonic acid (^SAnt)
  作者：Gowri Priya、Amol S. Kotmale、Debamitra Chakravarty、Vedavati G. Puranik、Pattuparambil R. Rajamohanan、Gangadhar J. Sanjayan

  DOI：10.1039/c4ob02421d

  日期：——

  This communication describes the utility of the conformationally restricted aromatic β-amino acid (2-aminobenzenesulfonic acid, ^SAnt) for inducing various folding interactions in short peptides.

  这份通讯描述了在短肽中引发各种折叠相互作用的构象受限芳香基β-氨基酸（2-氨基苯磺酸，SAnt）的实用性。
• Transesterification of α-Amino Esters Catalyzed by a Tetranuclear Zinc Cluster: Zn4(OCOCF3)6O
  作者：Takashi Ohshima、Kazushi Mashima、Yusuke Maegawa、Kazushi Agura、Yukiko Hayashi

  DOI：10.1055/s-0031-1290096

  日期：2012.1

  Transesterification of amino acid ester derivatives was developed using a tetranuclear zinc cluster, Zn4(OCOCF3)6O, as the catalyst. Because the reaction conditions were very mild, a variety of N-protective groups and functional groups on side chains were tolerated.

  氨基酸酯衍生物的转酯化反应采用四核锌簇 Zn4(OCOCF3)6O 作为催化剂得以发展。由于反应条件非常温和，多种 N-保护基团和侧链上的功能团均可耐受。