5-(甲氧基甲基)-1,2-恶唑-3-羧酸 | 95312-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(甲氧基甲基)-1,2-恶唑-3-羧酸
• 中文别名: 5-(甲氧基甲基)-1,2-噁唑-3-羧酸
• 英文名称: 5-methoxymethyl-3-isoxazolecarboxylic acid
• 英文别名: 5-Methoxymethyl Isoxazole 3-Carboxylic Acid；5-(Methoxymethyl)-1,2-oxazole-3-carboxylic acid
• CAS: 95312-32-6
• 化学式: C₆H₇NO₄
• mdl: MFCD14658810
• 分子量: 157.126
• InChiKey: ITLABBGKNGIQTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-4-methyl-N-[(2S)-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pentanamide 、 5-(甲氧基甲基)-1,2-恶唑-3-羧酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 5-(methoxymethyl)-N-[(2S)-4-methyl-1-[[(2S)-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopentan-2-yl]-1,2-oxazole-3-carboxamide
  参考文献：
  名称：

  Design and Synthesis of an Orally Bioavailable and Selective Peptide Epoxyketone Proteasome Inhibitor (PR-047)

  摘要：

  Proteasome inhibition has been validated as a therapeutic modality in the treatment of multiple myeloma and Non-Hodgkin's lymphoma. Carfilzomib, an epoxyketone currently undergoing clinical trials in malignant: diseases, is a highly selective inhibitor of the chymotrypsin-like (CT-L) activity of the proteasome: A chemistry effort was initiated to discover orally bioavailable analogues of carfilzomib, which would have potential for improved dosing flexibility and patient convenience over, intravenously administered agents. The lead. compound, 2-Me-5-thiazole-Ser(OMe)-Ser(OMe)-Phe-ketoepoxide (58) (PR-047), selectively inhibited CT-L activity of both the constitutive proteasome (beta 5) and immunoproteasome (LMP7) and demonstrated an absolute bioavailability of up to 39% in rodents and dogs. It was well tolerated with repeated oral. administration at doses resulting in > 80% proteasome inhibition in most tissues and elicited an antitumor response equivalent to intravenously administered carfilzomib in multiple human tumor xenograft and mouse syngeneic models. The favorable pharmacologic profile supports its further development for the treatment of malignant diseases.

  DOI：

  10.1021/jm801329v
• 作为产物：
  描述：

  5-(甲氧基甲基)-1,2-恶唑-3-羧酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以80%的产率得到5-(甲氧基甲基)-1,2-恶唑-3-羧酸
  参考文献：
  名称：

  New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents

  摘要：

  We prepared a series of N-aryl isoxazolecarboxamide, N-isoxazolylbenzamide compounds and derivatives and studied their anticonvulsant action in MES and MMS tests. Some of these reveal considerable activity, especially with respect to MES test. The disubstitution in the 2.6-position on the phenyl ring by two methyl groups would appear to be of primary importance for the activity. The amide bridge between the phenyl and isoxazolic rings, whether of the anilide or benzamide type, seems to show similar anticonvulsant behavior. We have selected the derivatives 8 (N-(2.6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide, 12 (N-(2,6-dimethylphenyl)-5-hydroxymethyl-3-isoxazolecarboxamide) and 51 (N-(5-methyl-3-isoxazolyl)-2.6-dimethylbenzamide) which are presently being studied in more extended pharmacological tests.

  DOI：

  10.1016/0223-5234(92)90137-p

文献信息

• PYRROLO [2, 3 -D]PYRIMIDINE DERIVATIVES AS INHIBITORS OF TROPOMYOSIN- RELATED KINASES
  申请人：Pfizer Limited

  公开号：EP2694509A1

  公开（公告）日：2014-02-12
• PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES AS INHIBITORS OF TROPOMYOSIN-RELATED KINASES
  申请人：Pfizer Limited

  公开号：EP2694509B1

  公开（公告）日：2016-05-18
• LONG-ACTING HIV PROTEASE INHIBITOR
  申请人：Shionogi & Co., Ltd.

  公开号：US20170253607A1

  公开（公告）日：2017-09-07

  The present invention provides useful compounds for HIV protease inhibitor. A compound represented by the following formula or its pharmaceutically acceptable salt: wherein ring A is R 4 is —Y—Z, hydrogen atom, halogen, hydroxy and the like, R 5 is hydrogen atom, halogen, hydroxy and the like, R 6 is each independently halogen, hydroxy, carboxy and the like, ring A may be substituted with said R 6 at any substitutable position(s), a is an integer of 0 to 7, ring B is substituted or unsubstituted aromatic carbocyclyl, or substituted or unsubstituted aromatic heterocyclyl, ring C is substituted or unsubstituted aromatic carbocyclyl, substituted or unsubstituted non-aromatic carbocyclyl, substituted or unsubstituted aromatic heterocyclyl, or substituted or unsubstituted non-aromatic heterocyclyl, R 1 is —Y—Z, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl and the like, R 2 and R 3 are each independently —Y—Z or hydrogen atom, provided that at least one of R 1 , R 2 , R 3 and R 4 is a group represented by formula: —Y—Z, Y is a bond, or a spacer of any combination selected from the group consisting of —O—, —S—, —NR 7 —, —C(═O)—, —SO—, —SO 2 —, —NR 7 —C(═O)—, —C(═O)—NR 7 —, —NR 7 —C(═O)—NR 7 —, —O—C(═O)—NR 7 —, —NR 7 —C(═O)—O—, —SO 2 —NR 7 —, —NR 7 —SO 2 —, substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted alkynylene, substituted or unsubstituted aromatic carbocyclediyl, substituted or unsubstituted non-aromatic carbocyclediyl, substituted or unsubstituted aromatic heterocyclediyl and substituted or unsubstituted non-aromatic heterocyclediyl, R 7 are each independently hydrogen atom, hydroxy, carboxy and the like, and Z is substituted aromatic carbocyclyl, substituted non-aromatic carbocyclyl, substituted aromatic heterocyclyl or substituted non-aromatic heterocyclyl.
• US5258397A
  申请人：——

  公开号：US5258397A

  公开（公告）日：1993-11-02
• US5464860A
  申请人：——

  公开号：US5464860A

  公开（公告）日：1995-11-07