tert-butyl uraconate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl uraconate
• 英文别名: Imidazole-5-propenoic acid, t-butyl(ester)；tert-butyl (E)-3-(1H-imidazol-5-yl)prop-2-enoate
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: TZSMDSAXWQQXSA-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  叔丁醇 、 反式尿刊酸 在 硫酸 作用下， 反应 20.0h， 生成 tert-butyl uraconate
  参考文献：
  名称：

  尿酸（UCA）甲酯与单线态氧和4-甲基-1,2,4-三唑啉-3,5-二酮（MTAD）的反应

  摘要：

  单线态氧加到顺式和反式尿酸甲酯（MUC）的咪唑环上，生成相应的2,5-内过氧化物，在低温下适度稳定，但在加热时分解，形成复杂的反应混合物。MTAD是一种单线态氧模拟物，可与顺式和反式-MUC反应，生成涉及烯烃侧链和咪唑环的C 4 -C 5双键的立体有择[4 + 2]反应产物。反式-MUC在25°C时形成1：2 MTAD加合物，而顺式异构体仅产生1：1加合物。立体定向性和没有MeOH捕获加合物的情况表明，这些反应可能不涉及开放或可捕获的偶极中间体。

  DOI：

  10.1016/j.tet.2006.07.108

文献信息

• SOLUBLE GUANYLATE CYCLASE STIMULATORS
  申请人：Berger Raphaelle

  公开号：US20170174693A1

  公开（公告）日：2017-06-22

  The invention provides compounds of the Formula (I) or a pharmaceutically acceptable salts thereof, wherein X, Y, Z, R 1 , R 2 , R 4 , R a , and the subscripts m, p, and q are as described herein. The compounds or their pharmaceutically acceptable salts can modulate the body's production of cyclic guanosine monophosphate (“cGMP”), and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention also provides pharmaceutical compositions which comprise compounds of Formula (I) or pharmaceutically acceptable salts thereof. The invention also relates to methods for use of the compounds or their pharmaceutically acceptable salts in the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose.

  该发明提供了Formula (I)的化合物或其药用盐，其中X、Y、Z、R1、R2、R4、Ra以及下标m、p和q如本文所述。这些化合物或其药用盐可以调节人体对环鸟苷酸单磷酸（“cGMP”）的产生，并通常适用于治疗和预防与扰乱的cGMP平衡相关的疾病。该发明还提供了包含Formula (I)的化合物或其药用盐的药物组合物。该发明还涉及使用这些化合物或其药用盐在治疗和预防上述疾病以及为此目的制备药物的方法。
• Soluble guanylate cyclase stimulators
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US10030027B2

  公开（公告）日：2018-07-24

  The invention provides compounds of the Formula (I) or a pharmaceutically acceptable salts thereof, wherein X, Y, Z, R1, R2, R4, Ra, and the subscripts m, p, and q are as described herein. The compounds or their pharmaceutically acceptable salts can modulate the body's production of cyclic guanosine monophosphate (“cGMP”), and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention also provides pharmaceutical compositions which comprise compounds of Formula (I) or pharmaceutically acceptable salts thereof. The invention also relates to methods for use of the compounds or their pharmaceutically acceptable salts in the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose.

  本发明提供了式（I）化合物 或其药学上可接受的盐，其中 X、Y、Z、R1、R2、R4、Ra 和下标 m、p 和 q 如本文所述。这些化合物或其药学上可接受的盐类可以调节人体产生的环磷酸鸟苷（"cGMP"），通常适用于治疗和预防与 cGMP 平衡紊乱有关的疾病。本发明还提供了包含式（I）化合物或其药学上可接受的盐的药物组合物。本发明还涉及将这些化合物或其药学上可接受的盐用于治疗和预防上述疾病的方法，以及为此目的制备药物的方法。
• 4-AMINO-2-(1H-PYRAZOLO[3,4-B]PYRIDIN-3-YL)-6-OXO-6,7-DIHYDRO-5H-PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES AND THE RESPECTIVE (1H-INDAZOL-3-YL) DERIVATIVES AS CGMP MODULATORS FOR TREATING CARDIOVASCULAR DISEASES
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3394067A1

  公开（公告）日：2018-10-31
• [EN] 4-AMINO-2-(1H-PYRAZOLO[3,4-B]PYRIDIN-3-YL)-6-OXO-6,7-DIHYDRO-5H-PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES AND THE RESPECTIVE (1H-INDAZOL-3-YL) DERIVATIVES AS CGMP MODULATORS FOR TREATING CARDIOVASCULAR DISEASES<br/>[FR] DÉRIVÉS DE 4-AMINO-2-(1H-PYRAZOLO[3,4-B]PYRIDIN-3-YL)-6-OXO-6,7-DIHYDRO-5H-PYRROLO[2,3-D]PYRIMIDINE ET DÉRIVÉS RESPECTIFS DE (1H-INDAZOL-3-YL) EN TANT QUE MODULATEURS CGMP POUR LE TRAITEMENT DE MALADIES CARDIOVASCULAIRES
  申请人：MERCK SHARP & DOHME

  公开号：WO2017112617A1

  公开（公告）日：2017-06-29

  The invention provides compounds of the Formula (I) or a pharmaceutically acceptable salts thereof, wherein X, Y, Z, R1, R2, R4, Ra, and the subscripts m, p, and q are as described herein. The compounds or their pharmaceutically acceptable salts can modulate the body's production of cyclic guanosine monophosphate ("cGMP"), and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance, such as cardiovascular disease, endothelial dysfunction, diastolic dysfunction, atherosclerosis, hypertension, heart failure, pulmonary hypertension (WHO groups I, II, III, IV), angina pectoris, thrombosis, restenosis, myocardial infarction, stroke, cardiac insufficiency, fibrosis, pulmonary hypertonia, erectile dysfunction, asthma, acute respiratory distress syndrome (ARDS), chronic kidney disease, cystic fibrosis, sickle cell anemia, scleroderma, Raynaud's Syndrome, diabetes, diabetic retinopathy, cirrhosis of the liver, chronic obstructive pulmonary disease (COPD), acute lung injury, pulmonary fibrosis or interstitial lung disease. The invention also provides pharmaceutical compositions which comprise compounds of Formula (I) or pharmaceutically acceptable salts thereof. The invention also relates to the compounds or their pharmaceutically acceptable salts for use in the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose.
• Reactions of urocanic acid (UCA) methyl esters with singlet oxygen and 4-methyl-1,2,4-triazoline-3,5-dione (MTAD)
  作者：Roberto Roa、Kevin E. O'Shea

  DOI：10.1016/j.tet.2006.07.108

  日期：2006.11

  Singlet oxygen adds to the imidazole ring of cis- and trans-methyl urocanate (MUC) to yield the corresponding 2,5-endoperoxides, which are modestly stable at low temperature but decompose upon warming to form complex reaction mixtures. MTAD, a singlet oxygen mimic, reacts with cis- and trans-MUC to yield stereospecific [4+2] reaction products involving the olefinic side chain and the C4–C5 double bond

  单线态氧加到顺式和反式尿酸甲酯（MUC）的咪唑环上，生成相应的2,5-内过氧化物，在低温下适度稳定，但在加热时分解，形成复杂的反应混合物。MTAD是一种单线态氧模拟物，可与顺式和反式-MUC反应，生成涉及烯烃侧链和咪唑环的C 4 -C 5双键的立体有择[4 + 2]反应产物。反式-MUC在25°C时形成1：2 MTAD加合物，而顺式异构体仅产生1：1加合物。立体定向性和没有MeOH捕获加合物的情况表明，这些反应可能不涉及开放或可捕获的偶极中间体。