N-allyl-N'-(2-hydroxy-1,1-bis-hydroxymethyl-ethyl)-urea | 90222-25-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N-allyl-N'-(2-hydroxy-1,1-bis-hydroxymethyl-ethyl)-urea
• 英文别名: N-Allyl-N'-(2-hydroxy-1,1-bis-hydroxymethyl-aethyl)-harnstoff；1-[1,3-Dihydroxy-2-(hydroxymethyl)propan-2-yl]-3-prop-2-enylurea；1-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-3-prop-2-enylurea
• CAS: 90222-25-6
• 化学式: C₈H₁₆N₂O₄
• 分子量: 204.226
• InChiKey: YVVSTNROKUIXFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-bromobenzyl)-4-methylphenyl]-D-glucitol 、 N-allyl-N'-(2-hydroxy-1,1-bis-hydroxymethyl-ethyl)-urea 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Discovery of a potent, low-absorbable sodium-dependent glucose cotransporter 1 (SGLT1) inhibitor (TP0438836) for the treatment of type 2 diabetes

  摘要：

  The design and synthesis of a novel class of low-absorbable SGLT1 inhibitors are described. To achieve low absorption in the new series, we performed an optimization study based on a strategy to increase TPSA. Fortunately, the optimization of an aglycon moiety and a side chain of the distal aglycon moiety led to the identification of compound 30b as a potent and low-absorbable SGLT1 inhibitor. Compound 30b showed a desirable PK profile in Sprague-Dawley (SD) rats and a favorable glucose-lowering effect in diabetic rats.

  DOI：

  10.1016/j.bmcl.2018.09.035
• 作为产物：
  描述：

  3-异氰酸丙烯 、 三羟甲基氨基甲烷 在 水 、 异丙醇 作用下， 生成 N-allyl-N'-(2-hydroxy-1,1-bis-hydroxymethyl-ethyl)-urea
  参考文献：
  名称：

  Notes - Reaction of Isocyanates with Tris-(hydroxymethyl) aminomethane

  摘要：

  DOI：

  10.1021/jo01099a607

文献信息

• C-PHENYL GLYCITOL COMPOUND
  申请人：Kakinuma Hiroyuki

  公开号：US20100022460A1

  公开（公告）日：2010-01-28

  Provided is a novel C-phenyl glycitol compound that may serve as a prophylactic or therapeutic agent for diabetes by inhibiting both SGLT1 activity and SGLT2 activity, thereby exhibiting a glucose absorption suppression action and a urine glucose excretion action. A C-phenyl glycitol compound represented by Formula (I) below or a pharmaceutically acceptable salt thereof or a hydrate thereof wherein R 1 and R 2 are the same or different and represent a hydrogen atom, a hydroxyl group, a C 1-6 alkyl group, a C 1-6 alkoxy group or a halogen atom, R 3 is a hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy group or a halogen atom, Y is a C 1-6 alkylene group, —O—(CH 2 )n— (n is an integer of 1 to 4) or a C 2-6 alkenylene group, provided that when Z is —NHC(═NH)NH 2 or —NHCON(R B )R C , n is not 1, Z is —CONHR A , —NHC(═NH)NH 2 or —NHCON(R B )R C ,

  提供的是一种新型C-苯基甘露醇化合物，可以作为预防或治疗糖尿病的药物，通过抑制SGLT1活性和SGLT2活性，从而表现出抑制葡萄糖吸收和尿液葡萄糖排泄的作用。该化合物表示为以下式子（I）的C-苯基甘露醇化合物，或其药学上可接受的盐或水合物，其中R1和R2相同或不同，表示氢原子、羟基、C1-6烷基、C1-6烷氧基或卤素原子，R3表示氢原子、C1-6烷基、C1-6烷氧基或卤素原子，Y表示C1-6烷基、-O-(CH2)n-（n为1至4的整数）或C2-6烯基烷基，但当Z为-NHC（=NH）NH2或-NHCON（RB）RC时，n不为1，Z为CONHRA，-NHC（=NH）NH2或-NHCON（RB）RC。
• C-PHENYL GLYCITOL COMPOUND FOR THE TREATMENT OF DIABETES
  申请人：TAISHO PHARMACEUTICAL CO., LTD

  公开号：EP2076503B1

  公开（公告）日：2013-07-17
• US7973012B2
  申请人：——

  公开号：US7973012B2

  公开（公告）日：2011-07-05
• Discovery of a potent, low-absorbable sodium-dependent glucose cotransporter 1 (SGLT1) inhibitor (TP0438836) for the treatment of type 2 diabetes
  作者：Shoichi Kuroda、Yohei Kobashi、Takahiro Oi、Hideaki Amada、Lisa Okumura-Kitajima、Fusayo Io、Koji Yamamto、Hiroyuki Kakinuma

  DOI：10.1016/j.bmcl.2018.09.035

  日期：2018.12

  The design and synthesis of a novel class of low-absorbable SGLT1 inhibitors are described. To achieve low absorption in the new series, we performed an optimization study based on a strategy to increase TPSA. Fortunately, the optimization of an aglycon moiety and a side chain of the distal aglycon moiety led to the identification of compound 30b as a potent and low-absorbable SGLT1 inhibitor. Compound 30b showed a desirable PK profile in Sprague-Dawley (SD) rats and a favorable glucose-lowering effect in diabetic rats.
• Notes - Reaction of Isocyanates with Tris-(hydroxymethyl) aminomethane
  作者：Roy Neville

  DOI：10.1021/jo01099a607

  日期：1958.5