({[(4-甲基苯基)磺酰基]氨基}乙酰基)氨基]乙酸 | 4703-34-8

• 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: ({[(4-甲基苯基)磺酰基]氨基}乙酰基)氨基]乙酸
• 英文名称: tosyl-glycyl-glycine
• 英文别名: N-(p-tosyl)glycylglycine；Ts-Gly-Gly-OH；N-[N-(toluene-4-sulfonyl)-glycyl]-glycine；N-[N-(Toluol-4-sulfonyl)-glycyl]-glycin；[({[(4-Methylphenyl)sulfonyl]amino}acetyl)amino]acetic acid；2-[[2-[(4-methylphenyl)sulfonylamino]acetyl]amino]acetic acid
• CAS: 4703-34-8
• 化学式: C₁₁H₁₄N₂O₅S
• mdl: MFCD02029744
• 分子量: 286.309
• InChiKey: LESILPKULCPDIL-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  ({[(4-甲基苯基)磺酰基]氨基}乙酰基)氨基]乙酸 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 水 为溶剂， 反应 16.0h， 生成 N_α-(Tosylglycylglycyl)-4-cyanphenylalanin
  参考文献：
  名称：

  Voigt; Wagner, Pharmazie, 1984, vol. 39, # 6, p. 379 - 381

  摘要：

  DOI：
• 作为产物：
  描述：

  Tosyl-thioglycyl-glycin 在 silver nitrate 作用下， 以 1,4-二氧六环 为溶剂， 生成 ({[(4-甲基苯基)磺酰基]氨基}乙酰基)氨基]乙酸
  参考文献：
  名称：

  Ried,W.; von der Emden,W., Justus Liebigs Annalen der Chemie, 1961, vol. 642, p. 128 - 133

  摘要：

  DOI：

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ROXADUSTAT AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉS DESTINÉS À LA PRÉPARATION DE ROXADUSTATE ET SES INTERMÉDIAIRES
  申请人：TEVA PHARMACEUTICALS INT GMBH

  公开号：WO2021026307A1

  公开（公告）日：2021-02-11

  The present invention provides new procedure and intermediates for the preparation of Roxadustat (1) comprising: (A) reducing a compound of formula 3', 3" or a mixture thereof: (3'), (3") wherein Pg is H or a OH protecting group, Ri is alkyl, aryl, or arylalkyl; R2, R3, R4, and Rs each independently represents alkyl, arylalkyl or alkenyl, or R2 and R3 and/or R4 and Rs, taken together with the nitrogen atom to which they are bonded, each independently form a ring selected from: (I), wherein R6 is H or CI- 6 alkyl; R7 is Ci to C6 alkyl and X- is an anion selected from the group consisting of halide, O-SO4 -R7 wherein R7 is Ci to C6 alkyl, or O-SO2 -Rs wherein Rs is phenyl, tolyl, methyl or trifluoromethyl; to form a compound of formula (2') wherein Pg is H or an OH protecting group, Ri is alkyl, aryl, or arylalkyl; and removing the Ri group and where present removing the OH protecting group; or (B) reducing a compound of formula 4', a compound of formula 4" or a mixture thereof: (4'), (4") wherein Pg is H or an OH protecting group; Ri is H, alkyl, aryl, or arylalkyl; R2, R3, R4, and R5 each independently represents alkyl, aryl, arylalkyl or alkenyl; or R2 is Ci-4 alkyl and R3 is Ci-4 alkoxy; or R2 and R3 and/or R4 and R5, taken together with the nitrogen atom to which they are bonded, each independently form a group selected from: (I) wherein R6 is H or CI-6 alkyl; and where Ri is not H, removing the Ri group, and, where present removing the OH protecting group.

  本发明提供了制备罗沙度胺（1）的新程序和中间体，包括：（A）还原式3'、3"或其混合物的化合物：（3'）、（3"），其中Pg为H或OH保护基，Ri为烷基、芳基或芳基烷基；R2、R3、R4和Rs分别独立表示烷基、芳基烷基或烯基，或者R2和R3和/或R4和Rs与它们连接的氮原子一起，各自独立地形成从选定的环中选择的环：（I），其中R6为H或CI-6烷基；R7为Ci至C6烷基，X-为从卤素、O-SO4-R7（其中R7为Ci至C6烷基）或O-SO2-Rs（其中Rs为苯基、甲苯基、甲基或三氟甲基）中选择的阴离子；形成式（2'）的化合物，其中Pg为H或OH保护基，Ri为烷基、芳基或芳基烷基；并去除Ri基团和如有的话去除OH保护基；或（B）还原式4'、4"或其混合物的化合物：（4'）、（4"），其中Pg为H或OH保护基；Ri为H、烷基、芳基或芳基烷基；R2、R3、R4和R5各自独立表示烷基、芳基、芳基烷基或烯基；或R2为Ci-4烷基，R3为Ci-4烷氧基；或者R2和R3和/或R4和R5与它们连接的氮原子一起，各自独立地形成从选定的组中选择的组：（I），其中R6为H或CI-6烷基；并且如果Ri不是H，则去除Ri基团，并在有的情况下去除OH保护基。
• Palladium-catalyzed base- and solvent-controlled chemoselective allylation of amino acids with allylic carbonates
  作者：Yang Zhou、Hang Chen、Panpan Lei、Chunming Gui、Haifeng Wang、Qiongjiao Yan、Wei Wang、Fener Chen

  DOI：10.1016/j.cclet.2022.02.029

  日期：2022.11

  of readily available amino acids, which is not only an oxygen nucleophile but also a nitrogen nucleophile, in palladium-catalyzed allylic substitution is realized under mild conditions. The chemoselectivity and multiple allylation are controlled by adjusting the reaction conditions. This represents the first example of this convenient access to valuable N,O-diallylated amino acids. Under the title conditions

  在温和条件下实现了在钯催化的烯丙基取代中利用容易获得的氨基酸，它不仅是氧亲核试剂，而且是氮亲核试剂。通过调节反应条件来控制化学选择性和多重烯丙基化。这代表了这种方便地获得有价值的N,O-二烯丙基化氨基酸的第一个例子。在标题条件下，一系列氨基酸（α-、β-、γ-）和二肽可以很容易地转化为相应的烯丙基产物，具有优异的产率（67 个实例，高达 99% 的产率）以及良好的功能性群体容忍度。
• Schoenheimer, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1926, vol. 154, p. 223
  作者：Schoenheimer

  DOI：——

  日期：——
• Otani, Acta Scholae Medicinalis Universitatis in Kioto, 1935, vol. 17, p. 175,176
  作者：Otani

  DOI：——

  日期：——
• Distress and disease status among patients with rheumatoid arthritis: Roles of coping styles and perceived responses from support providers
  作者：Kenneth W. Griffin、Ronald Friend、Alan T. Kaell、Ronald S. Bennett

  DOI：10.1207/s15324796abm2302_8

  日期：2001.5

  Previous research has shown that social support can have a beneficial impact on coping processes and psychological adjustment in patients with rheumatoid arthritis (RA). The association of individual coping styles and perceived responses from others to one's pain episodes with patients' distress and disease status over time was investigated. The sample consisted of 42 middle-aged patients with RA who were predominantly White (98%), female (64%), and married (88%). Participants completed surveys and their rheumatologist completed clinical assessments of patient disease status at 2 time points over a 9-month period Although punishing responses from others (e.g, getting irritated or angry when the patient is in pain) were perceived as relatively infrequent, they were associated with a patient coping style of focusing on and venting of negative emotion as well as elevated negative affect (NA). Findings also indicated that those who perceived punishing responses from close others and coped by venting negative emotions reported increased NA over time and were rated by their rheumatologist as having more severe RA disease status over time. Implications for psychosocial intervention and directions for future research are discussed.