3-去甲基甲氧苄啶 | 27653-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-去甲基甲氧苄啶
• 英文名称: 2,4-diamino-<3,4-dimethoxy-5-hydroxybenzyl>pyrimidine
• 英文别名: Trimethoprim；2,4-Diamino-5-(3-hydroxy-4,5-dimethoxy-benzyl)-pyrimidin；3-Demethyl-trimethoprim；5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenol；2,4-diamino-5-(3-hydroxy-4,5-dimethoxybenzyl)-pyrimidine；5-[(2,4-Diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenol
• CAS: 27653-69-6
• 化学式: C₁₃H₁₆N₄O₃
• 分子量: 276.295
• InChiKey: HWBPOLWLLFXEJY-UHFFFAOYSA-N

物化性质

• 熔点：
  >208°C (dec.)
• 沸点：
  572.2±60.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（非常轻微，加热）

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2,4-diamino-5-(3,4-dimethoxy-5-ethoxybenzyl)pyrimidine	110798-57-7	C15H20N4O3	304.349
  ——	3-[5-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenoxy]-propionic acid	82830-23-7	C16H20N4O5	348.359
  ——	[5-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenoxy]-acetic acid	82830-22-6	C15H18N4O5	334.332
  ——	4-[5-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenoxy]-butyric acid	82830-24-8	C17H22N4O5	362.385
  ——	7-[5-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenoxy]-heptanoic acid	82830-26-0	C20H28N4O5	404.466
  ——	[5-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenoxy]-acetic acid methyl ester	82830-27-1	C16H20N4O5	348.359
  ——	5-[5-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenoxy]-pentanoic acid methyl ester	82830-29-3	C19H26N4O5	390.439
  ——	4-[5-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenoxy]-butyric acid ethyl ester	82830-28-2	C19H26N4O5	390.439
  ——	6-[5-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenoxy]-hexanoic acid methyl ester	82830-30-6	C20H28N4O5	404.466
  ——	2,4-Diamino-5-(3,4-dimethoxy-5-(1-methyl-2-oxopropoxy)benzyl)pyrimidine	89446-24-2	C17H22N4O4	346.386

反应信息

• 作为反应物：
  描述：

  3-去甲基甲氧苄啶 在 盐酸 、 sodium hydroxide 、 potassium tert-butylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  二氢叶酸还原酶抑制剂的基于受体的设计：在一系列羧基取代的甲氧苄啶类似物中，通过晶体学确定的酶结合与酶亲和力的比较。

  摘要：

  通过使用大肠杆菌二氢叶酸还原酶（DHFR）的分子模型，设计了甲氧苄氨嘧啶（TMP）的类似物，该类似物并入了各种3'-羧基烷氧基部分，以便获得带正电荷的活性位点残基的离子相互作用。这些化合物中的某些已显示出对该酶的极高亲和力。例如，发现3'-（羧基戊基）氧基类似物对大肠杆菌DHFR的抑制作用是TMP的55倍（Ki = 0.024 nM，而TMP为1.32 nM）。大肠杆菌DHFR与TMP的二元复合物的X射线晶体学研究和该含酸系列化合物的两个成员定义了这些抑制剂的结合并显示了后两个抑制剂的羧基与Arg-57离子结合。

  DOI：

  10.1021/jm00381a008

文献信息

• Benzofuran derivatives and their use as antibacterial agents
  申请人：——

  公开号：US20040034047A1

  公开（公告）日：2004-02-19

  The invention relates to novel benzofuran derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as anti-infectives.

  该发明涉及新型苯并呋喃衍生物及其作为药物成分在制备药物组合物中的用途。该发明还涉及相关方面，包括制备化合物的过程、含有其中一种或多种化合物的药物组合物，特别是它们作为抗感染剂的用途。
• 2,4-diaminopyrimidines substituted with heterobicyclomethyl radicals at
  申请人：——

  公开号：US04761475A1

  公开（公告）日：1988-08-02

  Novel 2,4-diaminopyrimidines having substituted heterobicyclomethyl moieties in the 5-position have superior antibacterial properties.

  具有在5位上取代杂环甲基基团的新型2,4-二氨基嘧啶具有优越的抗菌性能。
• 2,4-diamino-(substituted-benzopyran(quinolyl,isoquinoly)methyl)pyrimidine
  申请人：——

  公开号：US04587342A1

  公开（公告）日：1986-05-06

  Novel 2,4-diaminopyrimidines having substituted heterobicyclomethyl moieties in the 5-position have superior antibacterial properties.

  在2,4-二氨基嘧啶的5位上具有取代杂环甲基基团的新型化合物具有优异的抗菌性能。
• 2,4-diamino-5-(substituted)pyrimidines, useful as antimicrobials
  申请人：Burroughs Wellcome Co.

  公开号：US04590271A1

  公开（公告）日：1986-05-20

  Compounds of the formula (II) ##STR1## or a salt, N-oxide or acyl derivative thereof, wherein Y is a group ##STR2## which is linked to the pyrimidinylmethyl moiety at the 1 or 7-position and is optionally substituted at the 2, 3, 4 or 6-position or at the 7-position when the linkage to the pyrimidinylmethyl moiety is at the 1-position wherein X is an oxygen or sulphur atom, a group CH.sub.2, a group S(O).sub.n where n=1 or 2, a group NR.sup.1 wherein R.sup.1 is hydrogen C.sub.1-4 alkyl or a group COR.sup.2 where R.sup.2 is hydrogen, C.sub.1-4 alkoxy or amino and the dotted line represents a single or double bond, have antimicrobial activity. Processes for making these compounds, pharmaceutical compositions containing them and the medical use of the compounds are also disclosed.

  化合物的公式（II）##STR1##或其盐，N-氧化物或酰基衍生物，其中Y是一个##STR2##的基团，它连接到嘧啶基甲基上的1或7位，并在2、3、4或6位或7位（当连接到嘧啶基甲基的位置为1位时）可选择地取代，其中X是氧或硫原子，CH.sub.2基团，S（O）.sub.n基团，其中n = 1或2，NR.sup.1基团，其中R.sup.1是氢C.sub.1-4烷基或COR.sup.2基团，其中R.sup.2是氢，C.sub.1-4烷氧基或氨基，虚线表示单键或双键，具有抗微生物活性。还公开了制备这些化合物的方法，含有它们的制药组合物以及化合物的医疗用途。
• Substituted pyrimidines, their synthesis and compositions containing them, their use in medicine and intermediates for making them
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0051879A2

  公开（公告）日：1982-05-19

  Compounds of the formula (1): or a salt, N-oxide or acyl derivative thereof, wherein is a six membered ring optionally containing a hetero atom double bonds, both the phenyl ring and the being optionally substituted except that when does not contain a hetero atom either or both the phenyl ring or must be substituted other than solely by a hydroxy group at the 4-position of the phenyl ring, and that there are no substituents attached to the atom of adjacent to the 6-position of the phenyl ring are useful in the treatment of bacterial infections. A process for preparing these compounds and novel chemical intermediates used in their preparation are disclosed as is the first medical use of the compounds of the formula (I) and pharmaceutical compositions containing them.

  式(1)化合物： 或其盐、N-氧化物或酰基衍生物，其中苯基环和苯基环均可被任选取代，但当不含有杂原子时，苯基环或苯基环均必须被取代，而不是仅被苯基环 4 位上的羟基取代，且与苯基环 6 位相邻的原子上不连接任何取代基。 本发明公开了制备这些化合物的工艺和用于制备这些化合物的新型化学中间体，以及式（I）化合物和含有这些化合物的药物组合物的首次医学用途。