tert-butyl N-[(2S)-1-[methoxy(methyl)amino]-5-[[[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]amino]-1-oxopentan-2-yl]carbamate | 183442-79-7

• 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
• 英文名称: tert-butyl N-[(2S)-1-[methoxy(methyl)amino]-5-[[[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]amino]-1-oxopentan-2-yl]carbamate
• CAS: 183442-79-7
• 化学式: C₂₈H₄₇N₅O₉S
• 分子量: 629.775
• InChiKey: RGRZYPKXTDSAEF-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  182
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[methoxy(methyl)amino]-5-[[[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]amino]-1-oxopentan-2-yl]carbamate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 phenacyl (2S)-1-[(2S)-2-acetamido-3-[[(E,4S)-4-[[(2R)-2-[[(3S)-2-hydroxy-6-[[[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]-3-phenylpropanoyl]amino]-5-(4-phenylmethoxyphenyl)pent-2-enoyl]amino]propanoyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Reassignment of stereochemistry and total synthesis of the thrombin inhibitor cyclotheonamide B

  摘要：

  DOI：

  10.1021/ja00042a053
• 作为产物：
  描述：

  N-叔丁氧羰基-N’-(4-甲氧基-2,3,6-三甲基苯磺酰基)精氨酸 在 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 tert-butyl N-[(2S)-1-[methoxy(methyl)amino]-5-[[[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]amino]-1-oxopentan-2-yl]carbamate
  参考文献：
  名称：

  Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

  摘要：

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.082

文献信息

• Beta-sheet mimetics and use thereof as inhibitors of biologically active peptides or proteins
  申请人：Kahn Michael

  公开号：US20060276408A1

  公开（公告）日：2006-12-07

  There are disclosed β-sheet mimetics and methods relating to the same for imparting or stabilizing the β-sheet structure of a peptide, protein or molecule. In one aspect, β-sheet mimetics are disclosed having utility as protease inhibitors in general and, more specifically, as serine protease inhibitors such as thrombin, elastase and Factor X inhibitors. In one embodiment, the β-sheet mimetic is a thrombin inhibitor.

  本发明揭示了β-折叠结构类似物及其相关方法，用于赋予或稳定肽、蛋白质或分子的β-折叠结构。在一个方面，本发明揭示了具有普遍作为蛋白酶抑制剂的效用的β-折叠结构类似物，更具体地说，是丝氨酸蛋白酶抑制剂，如凝血酶、弹性蛋白酶和X因子抑制剂。在一个实施例中，β-折叠结构类似物是凝血酶抑制剂。
• US7511039B2
  申请人：——

  公开号：US7511039B2

  公开（公告）日：2009-03-31
• Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B
  作者：Hiroyuki Konno、Kanako Kubo、Hidefumi Makabe、Emi Toshiro、Naoyuki Hinoda、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2007.06.082

  日期：2007.9

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.
• Reassignment of stereochemistry and total synthesis of the thrombin inhibitor cyclotheonamide B
  作者：Masahiko Hagihara、Stuart L. Schreiber

  DOI：10.1021/ja00042a053

  日期：1992.7